Yoshikai, N. : 2023 Science of Synthesis, 2023/3: Base-Metal Catalysis 2 DOI: 10.1055/sos-SD-239-00117
Base-Metal Catalysis 2

2.7 Cobalt-Catalyzed Cross-Coupling Reactions

More Information

Book

Editor: Yoshikai, N.

Authors: Adak, L. ; Aoki, S.; Banerjee, S. ; Bedford, R. B. ; Cheng, Z.; Costas, M. ; Gao, M.; Garai, B.; Ge, S. ; Gosmini, C. ; Hota, S. K.; Ilies, L. ; Jindal, A.; Kawanaka, Y.; Li, H. ; Li, M.; Liu, Q. ; Lu, Z. ; Mandal, R.; Matsunaga, S. ; Murarka, S. ; Nakamura, M. ; Nolla-Saltiel, R. ; Ollevier, T. ; Palone, A. ; Panda, S. P.; Sahoo, S.; Sang, J.; Schiltz, P.; Shenvi, R. A. ; Sundararaju, B. ; van der Puyl, V. ; Vicens, L. ; Wang, C. ; Wang, Y. ; Yang, X.; Yang, Y.; Yoshikai, N. ; Yoshino, T. ; Zeng, X. ; Zhang, G.

Title: Base-Metal Catalysis 2

Print ISBN: 9783132455030; Online ISBN: 9783132455054; Book DOI: 10.1055/b000000440

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

Science of Synthesis Reference Libraries



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.

Type: Multivolume Edition

 


Abstract

Transition-metal-catalyzed cross-coupling reactions have been an essential strategy for the construction of C—C bonds, including in the syntheses of pharmaceuticals and natural products, since the pioneering work of Heck, Negishi, and Suzuki, among others. Of the widely applied catalysts based on group 8–10 metals, economical cobalt salts have been shown to be advantageous as an alternative to other commonly used expensive and/or toxic catalysts. In this review, cobalt-catalyzed cross-coupling reactions of organometallic reagents, such as organomagnesium or organozinc derivatives, to achieve the formation of C—C bonds, are summarized. Furthermore, various methods for the cobalt-catalyzed reductive cross coupling of C—X/C—O electrophiles have also been reported for selective C—C bond formation, and these are also discussed.

 
  • 1 Marsden JA, Haley MM, In: Metal-Catalyzed Cross-Coupling Reactions de Meijere A, Diederich F. Wiley-VCH Weinheim, Germany 2004; 317
  • 2 Knochel P. Handbook of Functionalized Organometallics: Applications in Synthesis. Wiley-VCH; Weinheim, Germany 2005
  • 3 Johansson Seechurn CCC, Kitching MO, Colacot TJ, Snieckus V. Angew. Chem. Int. Ed. 2012; 51: 5062
  • 9 Gosmini C, Bégouin J.-M, Moncomble A. Chem. Commun. (Cambridge) 2008; 3221
  • 10 Amatore M, Aubert C, Malacria M, Petit M. Science of Synthesis Knowledge Updates 2012; 3: 1
  • 13 Rérat A, Gosmini C, In: Grignard Reagents and Transition Metal Catalysts Cossy J. De Gruyter Berlin 2016; 152
  • 19 Malapit CA, Visco MD, Reeves JT, Busacca CA, Howell AR, Senanayake CH. Adv. Synth. Catal. 2015; 357: 2199
  • 20 Gülak S, Stepanek O, Malberg J, Rad BR, Kotora M, Wolf R, Jacobi von Wangelin A. Chem. Sci. 2013; 4: 776
  • 21 Kuzmina OM, Steib AK, Fernandez S, Boudot W, Markiewicz JT, Knochel P. Chem.–Eur. J. 2015; 21: 8242
  • 26 Nicolas L, Izquierdo E, Angibaud P, Stansfield I, Meerpoel L, Reymond S, Cossy J. J. Org. Chem. 2013; 78: 11807
  • 27 Nicolas L, Angibaud P, Stansfield I, Bonnet P, Meerpoel L, Reymond S, Cossy J. Angew. Chem. Int. Ed. 2012; 51: 11101
  • 30 Barré B, Gonnard L, Campagne R, Reymond S, Marin J, Ciapetti P, Brellier M, Guérinot A, Cossy J. Org. Lett. 2014; 16: 6160
  • 32 Mao J, Liu F, Wang M, Wu L, Zheng B, Liu S, Zhong J, Bian Q, Walsh PJ. J. Am. Chem. Soc. 2014; 136: 17662
  • 33 Zhou Y, Wang L, Yuan G, Liu S, Sun X, Yuan C, Yang Y, Bian Q, Wang M, Zhong J. Org. Lett. 2020; 22: 4532
  • 38 Cahiez G, Chaboche C, Duplais C, Giulliani A, Moyeux A. Adv. Synth. Catal. 2008; 350: 1484
  • 42 Andersen C, Ferey V, Daumas M, Bernardelli P, Guérinot A, Cossy J. Org. Lett. 2019; 21: 2285
  • 46 Black HK, Horn DHS, Weedon BCL. J. Chem. Soc. 1954; 1704
  • 49 Shirakawa E, Sato T, Imazaki Y, Kimura T, Hayashi T. Chem. Commun. (Cambridge) 2007; 4513
  • 54 Dagousset G, François C, León T, Blanc R, Sansiaume-Dagousset E, Knochel P. Synthesis 2014; 46: 3133
  • 58 Metal-Catalyzed Cross-Coupling Reactions. Diederich F, Stang PJ. Wiley-VCH; Weinheim, Germany 1998
  • 65 Boudet N, Sase S, Sinha P, Liu C.-Y, Krasovskiy A, Knochel P. J. Am. Chem. Soc. 2007; 129: 12358
  • 66 Balkenhohl M, Ziegler DS, Desaintjean A, Bole LJ, Kennedy AR, Hevia E, Knochel P. Angew. Chem. Int. Ed. 2019; 58: 12898
  • 71 Amatore M, Gosmini C. Chem. Commun. (Cambridge) 2008; 5019
  • 72 Rérat A, Michon C, Agbossou-Niedercorn F, Gosmini C. Eur. J. Org. Chem. 2016; 4554
  • 77 Hernán-Gómez A, Herd E, Hevia E, Kennedy AR, Knochel P, Koszinowski K, Manolikakes SM, Mulvey RE, Schnegelsberg C. Angew. Chem. Int. Ed. 2014; 53: 2706
  • 81 Kazmierski I, Bastienne M, Gosmini C, Paris J.-M, Périchon J. J. Org. Chem. 2004; 69: 936
  • 82 Dorval C, Dubois E, Bourne-Branchu Y, Gosmini C, Danoun G. Adv. Synth. Catal. 2019; 361: 1777
  • 85 Liu X.-G, Zhou C.-J, Lin E, Han X.-L, Zhang S.-S, Li Q, Wang H. Angew. Chem. Int. Ed. 2018; 57: 13096
  • 87 Yeh V, Szabo WA, Applications of Transition Metal Catalysis in Drug Discovery and Development: An Industrial Perspective Crawley ML, Trost BM. Wiley Hoboken, NJ 2012; 165
  • 89 Hofmayer MS, Sunagatullina A, Brösamlen D, Mauker P, Knochel P. Org. Lett. 2020; 22: 1286
  • 90 Lorion MM, Koch V, Nieger M, Chen H.-Y, Lei A, Bräse S, Cossy J. Chem.–Eur. J. 2020; 26: 13163
  • 91 Liu F, Zhong J, Zhou Y, Gao Z, Walsh PJ, Wang X, Ma S, Hou S, Liu S, Wang M, Wang M, Bian Q. Chem.–Eur. J. 2018; 24: 2059
  • 93 Lawrence SA. Amines: Synthesis, Properties and Applications. Cambridge University Press; Cambridge 2004
  • 96 Toma G, Fujita K.-i, Yamaguchi R. Eur. J. Org. Chem. 2009; 4586
  • 100 Li J, Tan E, Keller N, Chen Y.-H, Zehetmaier PM, Jakowetz AC, Bein T, Knochel P. J. Am. Chem. Soc. 2019; 141: 98
  • 106 Metzger A, Piller FM, Knochel P. Chem. Commun. (Cambridge) 2008; 5824
  • 107 Benischke AD, Knoll I, Rérat A, Gosmini C, Knochel P. Chem. Commun. (Cambridge) 2016; 52: 3171
  • 108 Bégouin JM, Claudel S, Gosmini C. Synlett 2009; 3192
  • 111 Lutter FH, Grokenberger L, Spieß P, Hammann JM, Karaghiosoff K, Knochel P. Angew. Chem. Int. Ed. 2020; 59: 5546
  • 115 Quaternary Stereocenters: Challenges and Solutions for Organic Synthesis. Christoffers J, Baro A. Wiley-VCH; Weinheim, Germany 2005
  • 117 Palao E, López E, Torres-Moya I, de la Hoz A, Díaz-Ortiz Á, Alcázar J. Chem. Commun. (Cambridge) 2020; 56: 8210
  • 118 Dilauro G, Messa F, Bona F, Perrone S, Salomone A. Chem. Commun. (Cambridge) 2021; 57: 10564
  • 125 Mills LR, Gygi D, Ludwig JR, Simmons EM, Wisniewski SR, Kim J, Chirik PJ. ACS Catal. 2022; 12: 1905
  • 133 Knappke CEI, Grupe S, Gärtner D, Corpet M, Gosmini C, Jacobi von Wangelin A. Chem.–Eur. J. 2014; 20: 6828
  • 135 Pal S, Chowdhury S, Rozwadowski E, Auffrant A, Gosmini C. Adv. Synth. Catal. 2016; 358: 2431
  • 137 Czaplik WM, Mayer M, Jacobi von Wangelin A. Synlett 2009; 2931
  • 141 Amatore M, Gosmini C, Périchon J. Eur. J. Org. Chem. 2005; 989
  • 146 Ma W.-Y, Han G.-Y, Kang S, Pang X, Liu X.-Y, Shu X.-Z. J. Am. Chem. Soc. 2021; 143: 15930