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Practical, high-yield, regioselective, rhodium-catalyzed hydroformylation of functionalized .alpha.-olefins | Journal of the American Chemical Society
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    Practical, high-yield, regioselective, rhodium-catalyzed hydroformylation of functionalized .alpha.-olefins
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    Cite this: J. Am. Chem. Soc. 1993, 115, 5, 2066–2068
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    https://doi.org/10.1021/ja00058a079
    Published March 1, 1993

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    4. Patrick Wagner, Morgan Donnard, Nicolas Girard. Ligand-Controlled Regiodivergent Hydroformylation of Ynamides: A Stereospecific and Regioselective Access to 2- and 3-Aminoacroleins. Organic Letters 2019, 21 (21) , 8861-8866. https://doi.org/10.1021/acs.orglett.9b03566
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    6. Florent Péron, Stéphanie Riché, Brigitte Lesur, Marcel Hibert, Philippe Breton, Jean-Marie Fourquez, Nicolas Girard, Dominique Bonnet. Versatile Synthetic Approach for Selective Diversification of Bicyclic Aza-Diketopiperazines. ACS Omega 2018, 3 (11) , 15182-15192. https://doi.org/10.1021/acsomega.8b01752
    7. He Huang, Chenguang Yu, Yueteng Zhang, Yongqiang Zhang, Patrick S. Mariano, and Wei Wang . Chemo- and Regioselective Organo-Photoredox Catalyzed Hydroformylation of Styrenes via a Radical Pathway. Journal of the American Chemical Society 2017, 139 (29) , 9799-9802. https://doi.org/10.1021/jacs.7b05082
    8. Rachael Pittaway, José A. Fuentes, and Matthew L. Clarke . Diastereoselective and Branched-Aldehyde-Selective Tandem Hydroformylation–Hemiaminal Formation: Synthesis of Functionalized Piperidines and Amino Alcohols. Organic Letters 2017, 19 (11) , 2845-2848. https://doi.org/10.1021/acs.orglett.7b01049
    9. Wenlong Ren, Wenju Chang, Jie Dai, Yuan Shi, Jingfu Li, and Yian Shi . An Effective Pd-Catalyzed Regioselective Hydroformylation of Olefins with Formic Acid. Journal of the American Chemical Society 2016, 138 (45) , 14864-14867. https://doi.org/10.1021/jacs.6b10297
    10. Jaroslaw Mormul, Michael Mulzer, Tobias Rosendahl, Frank Rominger, Michael Limbach, and Peter Hofmann . Synthesis of Adipic Aldehyde by n-Selective Hydroformylation of 4-Pentenal. Organometallics 2015, 34 (16) , 4102-4108. https://doi.org/10.1021/acs.organomet.5b00538
    11. Caiyou Chen, Yu Qiao, Huiling Geng, and Xumu Zhang . A Novel Triphosphoramidite Ligand for Highly Regioselective Linear Hydroformylation of Terminal and Internal Olefins. Organic Letters 2013, 15 (5) , 1048-1051. https://doi.org/10.1021/ol400033k
    12. Robert Franke, Detlef Selent, and Armin Börner . Applied Hydroformylation. Chemical Reviews 2012, 112 (11) , 5675-5732. https://doi.org/10.1021/cr3001803
    13. Ranjan Jana and Jon A. Tunge . A Homogeneous, Recyclable Polymer Support for Rh(I)-Catalyzed C–C Bond Formation. The Journal of Organic Chemistry 2011, 76 (20) , 8376-8385. https://doi.org/10.1021/jo201476h
    14. Detlef Selent, Robert Franke, Christoph Kubis, Anke Spannenberg, Wolfgang Baumann, Burkard Kreidler, and Armin Börner . A New Diphosphite Promoting Highly Regioselective Rhodium-Catalyzed Hydroformylation. Organometallics 2011, 30 (17) , 4509-4514. https://doi.org/10.1021/om2000508
    15. Roderick W. Bates, K. Sivarajan, and Bernd F. Straub . A Synthesis of Pseudoconhydrine and Its Epimer via Hydroformylation and Dihydroxylation. The Journal of Organic Chemistry 2011, 76 (16) , 6844-6848. https://doi.org/10.1021/jo2008912
    16. Etienne Airiau, Nicolas Girard, Marianna Pizzeti, Jessica Salvadori, Maurizio Taddei, and André Mann . Hydroformylation of Alkenylamines. Concise Approaches toward Piperidines, Quinolizidines, and Related Alkaloids. The Journal of Organic Chemistry 2010, 75 (24) , 8670-8673. https://doi.org/10.1021/jo101776y
    17. Etienne Airiau, Thomas Spangenberg, Nicolas Girard, Bernhard Breit and André Mann . Short Access to (+)-Lupinine and (+)-Epiquinamide via Double Hydroformylation. Organic Letters 2010, 12 (3) , 528-531. https://doi.org/10.1021/ol902718q
    18. Javier Magano. Synthetic Approaches to the Neuraminidase Inhibitors Zanamivir (Relenza) and Oseltamivir Phosphate (Tamiflu) for the Treatment of Influenza. Chemical Reviews 2009, 109 (9) , 4398-4438. https://doi.org/10.1021/cr800449m
    19. Wen-Hua Chiou, Gau-Hong Lin, Che-Cheng Hsu, Stephen J. Chaterpaul and Iwao Ojima. Efficient Syntheses of Crispine A and Harmicine by Rh-Catalyzed Cyclohydrocarbonylation. Organic Letters 2009, 11 (12) , 2659-2662. https://doi.org/10.1021/ol900702t
    20. Ranjan Jana and Jon A. Tunge. A Homogeneous, Recyclable Rhodium(I) Catalyst for the Hydroarylation of Michael Acceptors. Organic Letters 2009, 11 (4) , 971-974. https://doi.org/10.1021/ol802927v
    21. Thomas Spangenberg, Bernhard Breit and André Mann . Hydroformylation of Homoallylic Azides: A Rapid Approach toward Alkaloids. Organic Letters 2009, 11 (2) , 261-264. https://doi.org/10.1021/ol802314g
    22. Guillaume Bélanger,, Robin Larouche-Gauthier,, Frédéric Ménard,, Miguel Nantel, and, Francis Barabé. Intramolecular Additions of Various π-Nucleophiles to Chemoselectively Activated Amides and Application to the Synthesis of (±)-Tashiromine. The Journal of Organic Chemistry 2006, 71 (2) , 704-712. https://doi.org/10.1021/jo052141v
    23. Gary E. Keck and, Anh P. Truong. Synthetic Studies on the Bryostatins:  Preparation of a Truncated BC-Ring Intermediate by Pyran Annulation. Organic Letters 2005, 7 (11) , 2149-2152. https://doi.org/10.1021/ol050511w
    24. Cong Liu and, Ross A. Widenhoefer. Palladium-Catalyzed Cyclization/Carboalkoxylation of Alkenyl Indoles. Journal of the American Chemical Society 2004, 126 (33) , 10250-10251. https://doi.org/10.1021/ja046810i
    25. Christopher J. Cobley,, Kelli Gardner,, Jerzy Klosin,, Céline Praquin,, Catherine Hill,, Gregory T. Whiteker, and, Antonio Zanotti-Gerosa, , Jeffrey L. Petersen, , Khalil A. Abboud. Synthesis and Application of a New Bisphosphite Ligand Collection for Asymmetric Hydroformylation of Allyl Cyanide. The Journal of Organic Chemistry 2004, 69 (12) , 4031-4040. https://doi.org/10.1021/jo040128p
    26. Robert D. Pike,, Bryn A. Reinecke,, Megan E. Dellinger,, Austin B. Wiles,, Jonathan D. Harper,, Jenine R. Cole,, Kimberly A. Dendramis,, Brian D. Borne,, Jeffrey L. Harris, and, William T. Pennington. Bicyclic Phosphite Esters from Pentaerythritol and Dipentaerythritol:  New Bridging Ligands in Organometallic and Inorganic Chemistry. Organometallics 2004, 23 (9) , 1986-1990. https://doi.org/10.1021/om049957r
    27. Norihiro Tokitoh. New Progress in the Chemistry of Stable Metallaaromatic Compounds of Heavier Group 14 Elements. Accounts of Chemical Research 2004, 37 (2) , 86-94. https://doi.org/10.1021/ar020093k
    28. Houston Byrd,, Jeremiah D. Harden,, Jennifer M. Butler,, Michael J. Jablonsky, and, Gary M. Gray. Nucleophilic Displacement Reactions of cis-Bis((2,2‘-biphenylylene)phosphochloridite ester)tetracarbonylmolybdenum(0). The First Example of an Unusual Hydrolysis Reaction Yielding Unsymmetrically Substituted Products. Organometallics 2003, 22 (21) , 4198-4205. https://doi.org/10.1021/om030411z
    29. Sai P. Shum,, Stephen D. Pastor,, Anthony D. DeBellis,, Paul A. Odorisio,, Lilibeth Burke,, Frank H. Clarke,, Grety Rihs,, Bogdan Piatek, and, Ronald K. Rodebaugh. Sterically Congested Tripodal Phosphites:  Conformational Analysis, Solid-State Polymorphism, Metal Complexation, and Application to the Asymmetric Hydrosilation of Ketones1. Inorganic Chemistry 2003, 42 (17) , 5097-5106. https://doi.org/10.1021/ic030099l
    30. Stephen D. Pastor,, Adam Carinci,, Nancy Khoury, and, David N. Rahni. The Synthesis and Conformation of Sterically Congested Seven-membered Rings Containing Tetracoordinate Germanium(IV):  Determination of the ΔG* For Ring Inversion1. Inorganic Chemistry 2001, 40 (15) , 3830-3832. https://doi.org/10.1021/ic010180t
    31. Piet W. N. M. van Leeuwen,, Paul C. J. Kamer,, Joost N. H. Reek, and, Peter Dierkes. Ligand Bite Angle Effects in Metal-catalyzed C−C Bond Formation. Chemical Reviews 2000, 100 (8) , 2741-2770. https://doi.org/10.1021/cr9902704
    32. Charles P. Casey,, Evelyn Lin Paulsen,, Eckart W. Beuttenmueller,, Bernd R. Proft,, Brock A. Matter, and, Douglas R. Powell. Electronically Dissymmetric DIPHOS Derivatives Give Higher n:i Regioselectivity in Rhodium-Catalyzed Hydroformylation Than Either of Their Symmetric Counterparts. Journal of the American Chemical Society 1999, 121 (1) , 63-70. https://doi.org/10.1021/ja982117h
    33. Charles P. Casey,, Evelyn Lin Paulsen,, Eckart W. Beuttenmueller,, Bernd R. Proft,, Lori M. Petrovich,, Brock A. Matter, and, Douglas R. Powell. Electron Withdrawing Substituents on Equatorial and Apical Phosphines Have Opposite Effects on the Regioselectivity of Rhodium Catalyzed Hydroformylation. Journal of the American Chemical Society 1997, 119 (49) , 11817-11825. https://doi.org/10.1021/ja9719440
    34. Godfried J. H. Buisman,, Lars A. van der Veen,, Paul C. J. Kamer, and, Piet W. N. M. van Leeuwen. Fluxional Processes in Asymmetric Hydroformylation Catalysts [HRhL⌒L(CO)2] Containing C2-Symmetric Diphosphite Ligands. Organometallics 1997, 16 (26) , 5681-5687. https://doi.org/10.1021/om970599k
    35. Robin B. Bedford,, Sergio Castillòn,, Penny A. Chaloner,, Carmen Claver,, Elena Fernandez,, Peter B. Hitchcock, and, Aurora Ruiz. Iridium Complexes of Orthometalated Triaryl Phosphites:  Synthesis, Structure, Reactivity, and Use as Imine Hydrogenation Catalysts. Organometallics 1996, 15 (19) , 3990-3997. https://doi.org/10.1021/om960239h
    36. Darren K. MacFarland and, Clark R. Landis. Synthesis and Characterization of Novel Ligands Designed for Secondary Interactions. Organometallics 1996, 15 (2) , 483-485. https://doi.org/10.1021/om950819z
    37. Stephen D. Pastor,, Sai P. Shum,, Anthony D. DeBellis,, Lilibeth P. Burke, and, Ronald K. Rodebaugh, , Frank H. Clarke, , Grety Rihs. Atomic Proximity Due to Molecular Congestion:  Rational Design of Bis(phosphite) Ligands by Restriction of Molecular Motion1. Inorganic Chemistry 1996, 35 (4) , 949-958. https://doi.org/10.1021/ic9509286
    38. Stephen D. Pastor,, Jonathan S. Rogers, and, M. Ali NabiRahni, , Edwin D. Stevens. Synthesis and Conformation of Chiral Eight-Membered 12H-Dibenzo[d,g][1,3,2]dioxaphosphocins1. Inorganic Chemistry 1996, 35 (7) , 2157-2161. https://doi.org/10.1021/ic951130p
    39. Luyun Zhang, Ding Liu, Huri Piao, Zhenhua Jia, Fen-Er Chen. A modified Bis-OPNN phosphorus ligand for Rh-catalyzed linear-selective hydroformylation of alkenes. Chinese Chemical Letters 2025, 36 (7) , 110640. https://doi.org/10.1016/j.cclet.2024.110640
    40. Viktor Söderholm, Marc Stajer, Carolin Savage, Leon Splittgerber, Dieter Vogt. Towards continuous Rh-hydroformylation of long chain alkenes: handling methodology for the long-term stability of Biphephos in a continuous reactor with an attached membrane separation unit. Catalysis Science & Technology 2025, 15 (2) , 592-604. https://doi.org/10.1039/D4CY01148A
    41. Mahtab Madani, Leonhard Schill, Blete Hulaj, Jakob Willner, Andreas Limbeck, Katharina Bica-Schröder, Rasmus Fehrmann, Anders Riisager. Extraction of rhodium from supported liquid-phase hydroformylation catalysts with supercritical carbon dioxide. Journal of CO2 Utilization 2024, 89 , 102968. https://doi.org/10.1016/j.jcou.2024.102968
    42. Yan Zong, Runtong Zhang, Baode Ma, Jianghua Peng, Chao Wu, Xiaomei Zou, Yu Qian, Gen-Qiang Chen, Xumu Zhang. Robust, scalable, and highly selective spirocyclic catalysts for industrial hydroformylation and isomerization-hydroformylation. Science Advances 2024, 10 (29) https://doi.org/10.1126/sciadv.ado9607
    43. Marie‐Hélène Pietraru, Nicolas Lentz, Louise Ponsard, Emmanuel Nicolas, Thibault Cantat. Catalytic Carbonylation of Acrylic Acid to Succinic Anhydride**. ChemCatChem 2023, 15 (21) https://doi.org/10.1002/cctc.202300720
    44. Peng Wang, Yaxin Wang, Helfried Neumann, Matthias Beller. Rhodium‐Catalyzed Formylation of Unactivated Alkyl Chlorides to Aldehydes. Chemistry – A European Journal 2023, 29 (8) https://doi.org/10.1002/chem.202203342
    45. Navjeet Kaur. Five-membered N-heterocycles–Part I. 2023, 1-35. https://doi.org/10.1016/B978-0-443-18941-8.00012-2
    46. Aurélien Coelho, Jean-Bernard Behr, Jean-Luc Vasse. Access to 5-bromopentanal and 6-bromohexanal derivatives via the bromination/hydrolysis of C,O-bis-zirconocenes generated from unsaturated Weinreb amides. Organic & Biomolecular Chemistry 2022, 20 (29) , 5803-5811. https://doi.org/10.1039/D2OB01073A
    47. Jinrong Zhang, Jin Li, Kechao Li, Jinyu Zhao, Zhengyi Yang, Lingbo Zong, Jianbin Chen, Cong-Xia Xie, Xiu-Xiu Zhao, Xiaofei Jia. A heterogeneous Rh/CPOL-BINAPa&PPh 3 catalyst for hydroformylation of olefins: chemical and DFT insights into active species and the roles of BINAPa and PPh 3. Catalysis Science & Technology 2022, 12 (11) , 3440-3446. https://doi.org/10.1039/D2CY00370H
    48. Runtong Zhang, Xin Yan, Shao-Tao Bai, Caiyou Chen, Bozhao Nan, Baode Ma, Jialin Wen, Xumu Zhang. Examination of Milstein Ru-PNN and Rh-Tribi/Tetrabi dual metal catalyst for isomerization-linear-hydroformylation of C4 raffinate and internal olefins. Green Synthesis and Catalysis 2022, 3 (1) , 40-45. https://doi.org/10.1016/j.gresc.2021.10.010
    49. Francesca Migliorini, Filippo Dei, Massimo Calamante, Samuele Maramai, Elena Petricci. Micellar Catalysis for Sustainable Hydroformylation. ChemCatChem 2021, 13 (12) , 2794-2806. https://doi.org/10.1002/cctc.202100181
    50. F. S. Golub’, V. A. Bolotov, V. N. Parmon. Modern Trends in the Processing of Linear Alpha Olefins into Technologically Important Products: Part I. Catalysis in Industry 2021, 13 (2) , 168-186. https://doi.org/10.1134/S2070050421020069
    51. Rui Sang, Yuya Hu, Rauf Razzaq, Ralf Jackstell, Robert Franke, Matthias Beller. State-of-the-art palladium-catalyzed alkoxycarbonylations. Organic Chemistry Frontiers 2021, 8 (4) , 799-811. https://doi.org/10.1039/D0QO01203C
    52. Daniele Fiorito, Simone Scaringi, Clément Mazet. Transition metal-catalyzed alkene isomerization as an enabling technology in tandem, sequential and domino processes. Chemical Society Reviews 2021, 50 (2) , 1391-1406. https://doi.org/10.1039/D0CS00449A
    53. F. S. Golub, V. A. Bolotov, V. N. Parmon. Modern trends in the processing of linear alpha olefins to technologically important products. Part 1. Kataliz v promyshlennosti 2020, 20 (6) , 433-455. https://doi.org/10.18412/1816-0387-2020-6-433-455
    54. Rui Sang, Carolin Schneider, Rauf Razzaq, Helfried Neumann, Ralf Jackstell, Matthias Beller. Palladium-catalyzed carbonylations of highly substituted olefins using CO-surrogates. Organic Chemistry Frontiers 2020, 7 (22) , 3681-3685. https://doi.org/10.1039/D0QO01164A
    55. Lachlan J.N. Waddell, Olivia F.B. Watts, Praphatsorn Saetang, Vatcharin Rukachaisirikul, Roderick W. Bates. Asperidine B: Total synthesis and structure correction. Tetrahedron Letters 2020, 61 (27) , 152078. https://doi.org/10.1016/j.tetlet.2020.152078
    56. O. Stelzer. BIPHEPHOS, biphephos. 2020https://doi.org/10.1002/9783527809080.cataz02030
    57. Carolin Schneider, Ralf Jackstell, Bert U. W. Maes, Matthias Beller. Palladium‐Catalyzed Alkoxycarbonylation of sec ‐Benzylic Ethers. European Journal of Organic Chemistry 2020, 2020 (8) , 932-936. https://doi.org/10.1002/ejoc.201901592
    58. Navjeet Kaur. Six-membered N-heterocycles. 2020, 1-64. https://doi.org/10.1016/B978-0-12-820282-1.00001-4
    59. Svenja Kloß, Detlef Selent, Anke Spannenberg, Robert Franke, Armin Börner, Muhammad Sharif. Effects of Substitution Pattern in Phosphite Ligands Used in Rhodium-Catalyzed Hydroformylation on Reactivity and Hydrolysis Stability. Catalysts 2019, 9 (12) , 1036. https://doi.org/10.3390/catal9121036
    60. Nermin Meriç, Nevin Arslan, Cezmi Kayan, Khadichakhan Rafikova, Alexey Zazybin, Aygul Kerimkulova, Murat Aydemir. Catalysts for the asymmetric transfer hydrogenation of various ketones from [3-[(2S)-2-[(diphenylphosphanyl)oxy]-3-phenoxypropyl]-1-methyl-1H-imidazol-3-ium chloride] and [Ru(η6-arene)(μ-Cl)Cl]2, Ir(η5-C5Me5)(μ-Cl)Cl]2 or [Rh(μ-Cl)(cod)]2. Inorganica Chimica Acta 2019, 492 , 108-118. https://doi.org/10.1016/j.ica.2019.04.016
    61. P.W.N.M. van Leeuwen. Rhodium-Catalyzed Hydroformylation. 2019https://doi.org/10.1016/B978-0-12-409547-2.11261-2
    62. Jui‐Chi Tsai, Yi‐Huei Lin, Guei‐Tang Chen, Yu‐Kai Gao, Yu‐Che Tseng, Chien‐Lun Kao, Wen‐Hua Chiou. Rhodium‐Catalyzed Domino Hydroformylation/Double‐Cyclization Reaction of Arylacetylenecarboxamides: Diastereoselectivity Studies and Application in the Synthesis of 1‐Azabicyclo[ x.y .0]alkanes. Chemistry – An Asian Journal 2018, 13 (21) , 3190-3197. https://doi.org/10.1002/asia.201801193
    63. Xiguang Zhao, Noemi Kedei, Alexandra Michalowski, Nancy E. Lewin, Gary E. Keck, Peter M. Blumberg. Deletion of the C26 Methyl Substituent from the Bryostatin Analogue Merle 23 Has Negligible Impact on Its Biological Profile and Potency. ChemBioChem 2018, 19 (10) , 1049-1059. https://doi.org/10.1002/cbic.201700677
    64. Ravinderpal Kour Sodhi, Satya Paul. An Overview of Metal Acetylacetonates: Developing Areas/Routes to New Materials and Applications in Organic Syntheses. Catalysis Surveys from Asia 2018, 22 (1) , 31-62. https://doi.org/10.1007/s10563-017-9239-9
    65. Cunyao Li, Wenlong Wang, Li Yan, Yunjie Ding. A mini review on strategies for heterogenization of rhodium-based hydroformylation catalysts. Frontiers of Chemical Science and Engineering 2018, 12 (1) , 113-123. https://doi.org/10.1007/s11705-017-1672-9
    66. Fengjin Wu, Leifeng Wang, Jiean Chen, David A. Nicewicz, Yong Huang. Direct Synthesis of Polysubstituted Aldehydes via Visible‐Light Catalysis. Angewandte Chemie 2018, 130 (8) , 2196-2200. https://doi.org/10.1002/ange.201712384
    67. Fengjin Wu, Leifeng Wang, Jiean Chen, David A. Nicewicz, Yong Huang. Direct Synthesis of Polysubstituted Aldehydes via Visible‐Light Catalysis. Angewandte Chemie International Edition 2018, 57 (8) , 2174-2178. https://doi.org/10.1002/anie.201712384
    68. Boy Cornils, Armin Börner, Robert Franke, Baoxin Zhang, Ernst Wiebus, Klaus Schmid. Hydroformylation. 2017, 23-90. https://doi.org/10.1002/9783527651733.ch2
    69. Duygu Elma Karakaş, Feyyaz Durap, Akın Baysal, Yusuf Selim Ocak, Khadichakhan Rafikova, Eda Çavuş Kaya, Alexey Zazybin, Hamdi Temel, Cezmi Kayan, Nermin Meriç, Murat Aydemir. Transfer hydrogenation reaction using novel ionic liquid based Rh(I) and Ir(III)-phosphinite complexes as catalyst. Journal of Organometallic Chemistry 2016, 824 , 25-32. https://doi.org/10.1016/j.jorganchem.2016.09.006
    70. Bojan P. Bondžić, Frank Rominger, Peter Hofmann. Synthesis, complexation behavior and catalytic performance of chelating bisphosphite ligands based on 9,10-brigded 9,10-dihydroanthracenes in Rh catalyzed hydroformylation of 4-pentenal. Journal of Molecular Catalysis A: Chemical 2016, 423 , 472-477. https://doi.org/10.1016/j.molcata.2016.07.049
    71. Cunyao Li, Kai Xiong, Li Yan, Miao Jiang, Xiangen Song, Tao Wang, Xingkun Chen, Zhuangping Zhan, Yunjie Ding. Designing highly efficient Rh/CPOL-bp&PPh 3 heterogenous catalysts for hydroformylation of internal and terminal olefins. Catalysis Science & Technology 2016, 6 (7) , 2143-2149. https://doi.org/10.1039/C5CY01655J
    72. Zongpeng Zhang, Caiyou Chen, Qian Wang, Zhengyu Han, Xiu-Qin Dong, Xumu Zhang. New tetraphosphite ligands for regioselective linear hydroformylation of terminal and internal olefins. RSC Advances 2016, 6 (18) , 14559-14562. https://doi.org/10.1039/C5RA23683E
    73. Cunyao Li, Li Yan, Lanlu Lu, Kai Xiong, Wenlong Wang, Miao Jiang, Jia Liu, Xiangen Song, Zhuangping Zhan, Zheng Jiang, Yunjie Ding. Single atom dispersed Rh-biphephos&PPh 3 @porous organic copolymers: highly efficient catalysts for continuous fixed-bed hydroformylation of propene. Green Chemistry 2016, 18 (10) , 2995-3005. https://doi.org/10.1039/C6GC00728G
    74. Pierre Regenass, Stéphanie Riché, Florent Péron, Didier Rognan, Marcel Hibert, Nicolas Girard, Dominique Bonnet. A step-economical multicomponent synthesis of 3D-shaped aza-diketopiperazines and their drug-like chemical space analysis. Organic & Biomolecular Chemistry 2016, 14 (37) , 8859-8863. https://doi.org/10.1039/C6OB01434H
    75. Caiyou Chen, Xiu-Qin Dong, Xumu Zhang. Recent progress in rhodium-catalyzed hydroaminomethylation. Organic Chemistry Frontiers 2016, 3 (10) , 1359-1370. https://doi.org/10.1039/C6QO00233A
    76. Qianhui Wu, Fanding Zhou, Xiao Shu, Lei Jian, Bin Xu, Xueli Zheng, Maolin Yuan, Haiyan Fu, Ruixiang Li, Hua Chen. Synthesis and application of PNP pincer ligands in rhodium-catalyzed hydroformylation of cycloolefins. RSC Advances 2016, 6 (109) , 107305-107309. https://doi.org/10.1039/C6RA24144A
    77. Masaru Akehi, Mariko Kawamoto, Tadakatsu Mandai. Chiral 1-(1,3-dithian-2-yl) prop-2-en-1-ols: new scaffolds for enantiopure α-hydroxyaldehydes. Tetrahedron 2015, 71 (37) , 6488-6498. https://doi.org/10.1016/j.tet.2015.05.039
    78. Nicolas Girard. Synthesis of Alkaloids Containing a Quinolizidine Core by Means of Strategies Based on a Hydroformylation Reaction. 2015, 235-252. https://doi.org/10.1016/B978-0-08-100023-6.00008-7
    79. U. Gellrich, T. Koslowski, B. Breit. Full kinetic analysis of a rhodium-catalyzed hydroformylation: beyond the rate-limiting step picture. Catalysis Science & Technology 2015, 5 (1) , 129-133. https://doi.org/10.1039/C4CY01209G
    80. Isao Ogino. Zeolite-supported Molecular Metal Complex Catalysts. 2014, 27-54. https://doi.org/10.1039/9781782628439-00027
    81. Murat Aydemir, Khadichakhan Rafikova, Nurzhamal Kystaubayeva, Salih Paşa, Nermin Meriç, Yusuf Selim Ocak, Alexey Zazybin, Hamdi Temel, Nevin Gürbüz, Ismail Özdemir. Ionic liquid based Ru(II)–phosphinite compounds and their catalytic use in transfer hydrogenation: X-ray structure of an ionic compound 1-chloro-3-(3-methylimidazolidin-1-yl)propan-2-ol. Polyhedron 2014, 81 , 245-255. https://doi.org/10.1016/j.poly.2014.05.079
    82. Anke Rost, Yvonne Brunsch, Arno Behr, Reinhard Schomäcker. Comparison of the Activity of a Rhodium‐Biphephos Catalyst in Thermomorphic Solvent Mixtures and Microemulsions. Chemical Engineering & Technology 2014, 37 (6) , 1055-1064. https://doi.org/10.1002/ceat.201400072
    83. Arno Behr, Thomas Seidensticker, Andreas J. Vorholt. Diester monomers from methyl oleate and proline via tandem hydroaminomethylation‐esterification sequence with homogeneous catalyst recycling using TMS‐technique. European Journal of Lipid Science and Technology 2014, 116 (4) , 477-485. https://doi.org/10.1002/ejlt.201300224
    84. Samir H. Chikkali, Jarl Ivar van der Vlugt, Joost N.H. Reek. Hybrid diphosphorus ligands in rhodium catalysed asymmetric hydroformylation. Coordination Chemistry Reviews 2014, 262 , 1-15. https://doi.org/10.1016/j.ccr.2013.10.024
    85. Roderick W. Bates, Nur Filza bte Mohamed Aslam, Chi H. Tang, Oliver Simon. A synthesis of 5-hydroxysedamine using hydroformylation. Tetrahedron 2014, 70 (12) , 2134-2140. https://doi.org/10.1016/j.tet.2014.02.001
    86. Elena V. Gusevskaya, Jhonny Jiménez‐Pinto, Armin Börner. Hydroformylation in the Realm of Scents. ChemCatChem 2014, 6 (2) , 382-411. https://doi.org/10.1002/cctc.201300474
    87. B. Breit, L. Diab. 4.18 Hydroformylation and Related Carbonylation Reactions of Alkenes, Alkynes, and Allenes. 2014, 995-1053. https://doi.org/10.1016/B978-0-08-097742-3.00424-9
    88. Pierre Regenass, Jean-François Margathe, André Mann, Jean Suffert, Marcel Hibert, Nicolas Girard, Dominique Bonnet. Diastereoselective synthesis of novel aza-diketopiperazines via a domino cyclohydrocarbonylation/addition process. Chem. Commun. 2014, 50 (68) , 9657-9660. https://doi.org/10.1039/C4CC03660C
    89. Caiyou Chen, Pan Li, Zhoumi Hu, Heng Wang, Huaisu Zhu, Xinquan Hu, Yan Wang, Hui Lv, Xumu Zhang. Synthesis and application of a new triphosphorus ligand for regioselective linear hydroformylation: a potential way for the stepwise replacement of PPh 3 for industrial use. Org. Chem. Front. 2014, 1 (8) , 947-951. https://doi.org/10.1039/C4QO00132J
    90. M. Karaman, S. Irisli, O. Büyükgüngör. Structure analysis of O,O’-propane-1,3-diyl bis[diphenyl(phosphinothioate)]. Crystallography Reports 2013, 58 (7) , 1088-1090. https://doi.org/10.1134/S1063774513080051
    91. Urs Gellrich, Daniel Himmel, Markus Meuwly, Bernhard Breit. Realistic Energy Surfaces for Real‐World Systems: An IMOMO CCSD(T):DFT Scheme for Rhodium‐Catalyzed Hydroformylation with the 6‐DPPon Ligand. Chemistry – A European Journal 2013, 19 (48) , 16272-16281. https://doi.org/10.1002/chem.201302132
    92. Iwao Ojima, Alexandra A. Athan, Stephen J. Chaterpaul, Joseph J. Kaloko, Yu‐Han Gary Teng. Organorhodium Chemistry. 2013, 135-318. https://doi.org/10.1002/9781118651421.ch2
    93. Yaser A. El‐Badry, Ahmed F. El‐Farargy, Peter Eilbracht. Tandem Hydroformylation/Reductive Amination of 3‐Allyl‐2‐methylquinazolin‐4(3 H )‐one. Helvetica Chimica Acta 2013, 96 (9) , 1782-1792. https://doi.org/10.1002/hlca.201200237
    94. Roderick W. Bates, Sivarajan Kasinathan. Synthesis of azimic acid using hydroformylation. Tetrahedron 2013, 69 (14) , 3088-3092. https://doi.org/10.1016/j.tet.2013.01.060
    95. Roderick W. Bates, Sivarajan Kasinathan. Hydroformylation in Natural Product Synthesis. 2013, 187-223. https://doi.org/10.1007/128_2013_428
    96. Luca Gonsalvi, Antonella Guerriero, Eric Monflier, Frédéric Hapiot, Maurizio Peruzzini. The Role of Metals and Ligands in Organic Hydroformylation. 2013, 1-47. https://doi.org/10.1007/128_2013_430
    97. Roberta Settambolo. Rhodium-Catalyzed Hydroformylation in Fused Azapolycycles Synthesis. 2013, 151-186. https://doi.org/10.1007/128_2013_432
    98. I. Ojima, A. Athan, C. Commandeur, W.-H. Chiou. Amidocarbonylation, Cyclohydrocarbonylation, and Related Reactions. 2013https://doi.org/10.1016/B978-0-12-409547-2.03980-9
    99. Xiaofei Jia, Zheng Wang, Chungu Xia, Kuiling Ding. Novel spiroketal-based diphosphite ligands for hydroformylation of terminal and internal olefins. Catalysis Science & Technology 2013, 3 (8) , 1901. https://doi.org/10.1039/c3cy00187c
    100. Xiaofei Jia, Zheng Wang, Chungu Xia, Kuiling Ding. Spiroketal‐Based Phosphorus Ligands for Highly Regioselective Hydroformylation of Terminal and Internal Olefins. Chemistry – A European Journal 2012, 18 (48) , 15288-15295. https://doi.org/10.1002/chem.201203042
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    Cite this: J. Am. Chem. Soc. 1993, 115, 5, 2066–2068
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