Review
Cross-Coupling Reactions Of Organoboranes: An Easy Way To Construct CC Bonds (Nobel Lecture)†
Prof. Akira Suzuki,
Corresponding Author
Prof. Akira Suzuki
Hokkaido University, Sapporo, Hokkaido (Japan)
Hokkaido University, Sapporo, Hokkaido (Japan)Search for more papers by this authorProf. Akira Suzuki,
Corresponding Author
Prof. Akira Suzuki
Hokkaido University, Sapporo, Hokkaido (Japan)
Hokkaido University, Sapporo, Hokkaido (Japan)Search for more papers by this author†
Copyright© The Nobel Foundation 2010. We thank the Nobel Foundation, Stockholm, for permission to print this lecture.
Graphical Abstract
Tools for chemists: The Nobel Prize in Chemie 2010 was awarded for research on palladium-catalyzed cross-coupling in organic synthesis. Two of the Laureates, A. Suzuki and E. Negishi, report here first hand on the historical development and the current status of this research.
References
- 1 Metal-Catalyzed Cross-Coupling Reactions (Eds.: ), Wiley-VCH, Weinheim, 1998.
- 2“Approximate Self Consistent Field Molecular Orbital Calculations on the Complexes of Trimethylboron, Boron Trichloride, Trimethylaluminium, Alane and Aluminium Trichloride with Trimethylamine”: O. Gropen, A. Haaland, Acta Chem. Scand. 1973, 27, 521–527.
- 3“Stereo- and Regiospecific Syntheses to Provide Conjugated (E,Z)- and (Z,Z)-Alkadienes, and Arylated (Z)-Alkenes in Excellent Yields via the Palladium-Catalyzed Cross-Coupling reactions of (Z)-1-alkenylboronates with 1-Bromoalkenes and Aryl iodides”: N. Miyaura, M. Satoh, A. Suzuki, Tetrahedron Lett. 1986, 27, 3745–3748.
- 4“Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds”: N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457–2483.
- 5“Cross-coupling reactions of organoboron compounds with organic halides”: A. Suzuki in Metal-Catalyzed Cross-Coupling Reactions (Eds.: ), Wiley-VCH, Weinheim, 1998, pp. 49–98.
10.1002/9783527612222 Google Scholar
- 6“Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles, 1995–1998”: A. Suzuki, J. Organomet. Chem. 1999, 576, 147–168.
- 7“The Suzuki Reaction with Arylboron Compounds in Arene Chemistry”: A. Suzuki in Modern Arene Chemistry (Ed.: ), Wiley-VCH, Weinheim, 2002, pp. 53–106.
10.1002/3527601767.ch3 Google Scholar
- 8“Total Synthesis of a Fully Protected Palytoxin Carboxylic Acid”: Y. Kishi, R. W. Armstrong, J. M. Beau, S. H. Cheon, H. Fujioka, W. H. Ham, L. D. Hawkins, H. Jin, S. H. Kang, M. J. Martinelli, W. W. McWhorter, Jr., M. Mizuno, M. Nakata, A. E. Stutz, F. X. Talamas, M. Taniguchi, J. A. Tino, K. Ueda, J.-i. Uenishi, J. B. White, M. Yonaga, J. Am. Chem. Soc. 1989, 111, 7525–7530; “Total Synthesis of Palytoxin Carboxylic Acid and Palytoxin Amide”: R. W. Armstrong, J.-M. Beau, S. H. Cheon, W. J. Christ, H. Fujioka, W.-H. Ham, L. D. Hawkins, H. J. Sung, S. H. Kang, Y. Kishi, M. J. Martinelli, W. W. MacWhorter, Jr., M. Mizuno, J. A. Tino, K. Ueda, J.-i. Uenishi, J. B. White, M. Yonaga, J. Am. Chem. Soc. 1989, 111, 7530–7533.
- 9“Total Synthesis of Lucilactaene, A Cell Cycle Inhibitor Active in p53-Inactive Cells”: R. S. Coleman, M. C. Walczak, E. L. Campbell, J. Am. Chem. Soc. 2005, 127, 16038–16039.
- 10“Novel and Convenient Method for the Stereo- and Regiospecific Synthesis of Conjugated Alkadienes and Alkenynes via the Palladium-Catalyzed Cross-Coupling Reaction of 1-Alkenylboranes with Bromoalkenes and Bromoalkynes”: N. Miyaura, K. Yamada, H. Suginome, A. Suzuki, J. Am. Chem. Soc. 1985, 107, 972–980.
- 11“Palladium-Catalyzed Cross-Coupling Reaction of (1-Ethoxy-1-alken-2-yl)boranes With ortho-Functionalized Iodoarenes. A Novel and Convenient Synthesis of Benzo-Fused Heteroaromatic Compounds”: M. Satoh, N. Miyaura, A. Suzuki, Synthesis 1987, 373–377.
- 12“The Palladium-Catalyzed Cross-Coupling Reaction of Phenylboronic Acid with Haloarenes in the Presence of Bases”: N. Miyaura, T. Yanagi, A. Suzuki, Synth. Commun. 1981, 11, 513–519.
- 13“Fluoride-Mediated Boronic Acid Coupling Reactions”: S. W. Wright, D. L. Hageman, L. D. McClure, J. Org. Chem. 1994, 59, 6095–6097.
- 14“Suzuki Coupling”: A. Suzuki, Organic Syntheses via Boranes, Vol. 3, Aldrich, USA, 2003.
- 15“Synthesis of Sterically Hindered Biaryls via the Palladium-Catalyzed Cross-Coupling Reaction of Arylboronic Acids or their Esters with Haloarenes”: T. Watanabe, N. Miyaura, A. Suzuki, Synlett 1992, 207–210.
- 16“Heterolytic Cleavage of Main Group Metal-Carbon Bonds”: M. H. Abraham, P. L. Grellier in The Chemistry of the Metal-Carbon Bond, Vol. 2 (Eds.: ), Wiley, New York, 1985, pp. 25–150.
10.1002/9780470771747.ch2 Google Scholar
- 17“A Highly Active Suzuki Catalyst for the Synthesis of Sterically Hindered Biaryls: Novel Ligand Coordination”: J. Yin, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 1162–1163.
- 18“Versatile Catalysts for the Suzuki Cross-Coupling of Arylboronic Acids with Aryl and Vinyl Halides and Triflates under Mild Conditions”: A. F. Littke, C. Dai, G. C. Fu, J. Am. Chem. Soc. 2000, 122, 4020–4028.
- 19“Highly Active Palladium Catalysts for Suzuki Coupling Reactions”: J. P. Wolfe, R. A. Singer, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 9550–9561.
- 20“A New Highly Efficient Catalyst System for the Coupling of Nonactivated and Deactivated Aryl Chlorides with Arylboronic Acids”: A. Zapf, A. Ehrentraut, M. Beller, Angew. Chem. 2000, 112, 4315–4317;
10.1002/1521-3757(20001117)112:22<4315::AID-ANGE4315>3.0.CO;2-L Google ScholarAngew. Chem. Int. Ed. 2000, 39, 4153–4155.10.1002/1521-3773(20001117)39:22<4153::AID-ANIE4153>3.0.CO;2-T CAS PubMed Web of Science® Google Scholar
- 21“A Convergent Total Synthesis of the Michellamines”: G. Bringmann, R. Götz, P. A. Keller, R. Walter, M. R. Boyd, F. Lang, A. Garcia, J. J. Walsh, L. Tellitu, K. V. Bhaskar, T. R. Kelly, J. Org. Chem. 1998, 63, 1090–1097.
- 22“A Suzuki Coupling-Macrolactamization Approach to the AB-COD Bicyclic System of Vancomycin”: K. C. Nicolaou, J. M. Ramanjulu, S. Natarajan, S. Bräse, H. Li, C. N. C. Boddy, F. Rübsam, Chem. Commun. 1997, 1899–1990.
- 23“Total Synthesis of Vancomycin-Part 3: Synthesis of the Aglycon”: K. C. Nicolaou, A. E. Koumbis, M. Takayanagi, S. Natarajan, N. F. Jain, T. Bando, H. Li, R. Hughes, Chem. Eur. J. 1999, 5, 2622–2647.
10.1002/(SICI)1521-3765(19990903)5:9<2622::AID-CHEM2622>3.0.CO;2-T CAS Web of Science® Google Scholar
- 24“Syntheses of Phenothiazinylboronic Acid Derivatives—Suitable Starting Points for the Construction of Redox Active Materials”: C. S. Krämer, T. J. Zimmermann, M. Sailer, J. J. Müller, Synthesis 2002, 1163–1170.
- 25“Head-to-Tail Regioregular Oligothiophene-Functionalized 9,9′-Spirobifluorene Derivatives. 1. Synthesis”: J. Pei, J. Ni, X.-H. Zhou, X.-Y. Cao, Y.-H. Lai, J. Org. Chem. 2002, 67, 4924–4936.
- 26“Boronic Ester as a Linker System for Solid Phase Synthesis”: B. Carboni, C. Pourbaix, F. Carreaux, H. Deleuze, B. Maillard, Tetrahedron Lett. 1999, 40, 7979–7983.
- 27“Soluble poly(para-phenylene)s. 1. Extension of the Yamamoto synthesis to dibromobenzenes substituted with flexible side chains”: M. Rehahn, A. D. Schlüter, G. Wegner, W. Feast, Polymer 1989, 30, 1054–1059.
- 28“The Tenth Anniversary of Suzuki Polycondensation (SPC)”: A. D. Schlüter, J. Polym. Sci. Part A 2001, 39, 1533–1556.
- 29“Polymeric Alkoxy PBD [2-(4-Biphenylyl)-5-Phenyl-1,3,4-Oxadiazole] for Light-Emitting Diodes”: C. Wang, M. Kilitzirak, L.-O. Palsson, M. R. Bryce, A. P. Monkman, D. W. Samuel I, Adv. Funct. Mater. 2001, 11, 47–50.
- 30“Palladium-Catalyzed Cross-Coupling Reactions of B-alkyl-9-BBN or Trialkylboranes with Aryl and 1-Alkenyl halides”: N. Miyaura, T. Ishiyama, M. Ishikawa, A. Suzuki, Tetrahedron Lett. 1986, 27, 6369–6372.
- 31“Palladium-Catalyzed Inter- and Intramolecular Cross-Coupling Reactions of B-alkyl-9-borabicyclo[3.3.1]nonane Derivatives with 1-Halo-1-alkenes or Haloarenes. Syntheses of functionalized alkenes, arenes, and cycloalkenes via a Hydroboration-Coupling Sequence”: N. Miyaura, T. Ishiyama, H. Sasaki, M. Ishikawa, M. Satoh, A. Suzuki, J. Am. Chem. Soc. 1989, 111, 314–321.
- 32“Total Synthesis of (−)-Epothilone B: An Extension of the Suzuki Coupling Method and Insights into Structure-Activity Relationships of the Epothilones”: D.-S. Su, D. Meng, P. Bertinato, A. Balog, E. J. Sorensen, S. J. Danishefsky, Y.-H. Zheng, T.-C. Chou, L. He, S. B. Horwitz, Angew. Chem. 1997, 109, 775–777; Angew. Chem. Int. Ed. Engl. 1997, 36, 757–759.
- 33“A Novel Aldol Condensation with 2-Methyl-4-pentenal and Its Application to an Improved Total Synthesis of Epothilone B”: A. Balog, C. Harris, K. Savin, X.-G. Zhang, T. C. Chao, S. J. Danishefsky, Angew. Chem. 1998, 110, 2821–2824;
10.1002/(SICI)1521-3757(19981002)110:19<2821::AID-ANGE2821>3.0.CO;2-G Google ScholarAngew. Chem. Int. Ed. 1998, 37, 2675–2678.10.1002/(SICI)1521-3773(19981016)37:19<2675::AID-ANIE2675>3.0.CO;2-O CAS Web of Science® Google Scholar
- 34“Total Synthesis of (−)-Epothilone A”: A. Balog, D. Meng, T. Kamenecka, P. Bertinato, D. Su, E. J. Sorensen, S. J. Danishefsky, Angew. Chem. 1996, 108, 2976–2978;
10.1002/ange.19961082318 Google ScholarAngew. Chem. Int. Ed. Engl. 1996, 35, 2801–2803.
- 35“Total Syntheses of Epothilones A and B”: D. Meng, P. Bertinato, A. Balog, D.-S. Su, T. Kamenecka, E. J. Sorensen, S. J. Danishefsky, J. Am. Chem. Soc. 1997, 119, 10073–10092.
- 36“New strategy for convergent synthesis of trans-fused polyether frameworks based on palladium-catalyzed suzuki cross-coupling reaction”: M. Sasaki, H. Fuwa, M. Inoue, K. Tachibana, Tetrahedron Lett. 1998, 39, 9027–9030.
- 37“Alkynylboranes in the Suzuki–Miyaura coupling”: J. A. Soderquist, K. Matos, A. Rane, J. Ramos, Tetrahedron Lett. 1995, 36, 2401–2402.
- 38“Palladium-Catalyzed Arylation of Polar Organometallics Mediated by 9-Methoxy-9-borabicyclo[3.3.1]nonane: Suzuki Reactions of Extended Scope”: A. Fürstner, G. Seidel, Tetrahedron 1995, 51, 11165–11178.
- 39“Development of the Suzuki–Miyaura Cross-Coupling Reaction: Use of Air-Stable Potassium Alkynyltrifluoroborates in Aryl Alkynylations”: G. A. Molander, B. W. Katona, F. Machrouhi, J. Org. Chem. 2002, 67, 8416–8423.
- 40“A Reassessment of the Transition-Metal Free Suzuki-Type Coupling Methodology”: R. K. Arvela, N. E. Leadbeater, M. S. Sangi, V. A. Williams, P. Granados, R. D. Singer, J. Org. Chem. 2005, 70, 161–168.
- 41“Solventless Suzuki Coupling Reactions on Palladium-Doped KF/Al2O3”: G. W. Kabalka, R. M. Pagni, C. M. Hair, Org. Lett. 1999, 1, 1423–1425.
- 42“Palladium Catalysed Suzuki Cross-Coupling Reactions in Ambient Temperature Ionic Liquids”: C. J. Mathews, P. J. Smith, T. Welton, Chem. Commun. 2000, 1249–1250.
