Download PDF
Yu, J.-Q.: 2015 Science of Synthesis, 3b: Catalytic Transformations via C-H Activation Vol. 2 DOI: 10.1055/sos-SD-218-00023
Catalytic Transformations via C—H Activation 2

2.3 C—C Bond Formation Using Carbenes

More Information

Book

Editor: Yu, J.-Q.

Authors: Carreira, E. M.; Decicco, C. P.; Fuerstner, A.; Koch, G.; Molander, G. A.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.

Title: Catalytic Transformations via C-H Activation Vol. 2

Print ISBN: 9783132057210; Online ISBN: 9783132404137; Book DOI: 10.1055/b-004-129675

2015 © 2015 Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry

Science of Synthesis Reference Libraries



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Type: Multivolume Edition

Also available at
 


Abstract

Transition-metal-catalyzed carbene C—H insertion has been developed as one of the most direct and effective methods for the construction of C—C bonds from C—H bonds. During the past two decades, a number of transition-metal-based catalytic systems have been established for asymmetric C—H functionalization via carbene insertion. Synthetically useful systems have been developed to functionalize C—H bonds in both intermolecular and intramolecular fashions. In this chapter, highly selective and practical catalytic systems for stereoselective C—H functionalization via catalytic carbene transfer are summarized. Literature reports are classified and discussed according to the type of C—H bond. This review focuses mainly on the issue of stereoselectivity, particularly on enantioselectivity.

Key words

asymmetric synthesis - C—H functionalization - transition-metal catalysis - diazo reagents - metal carbenes - dirhodium(II) complexes
 
  • 1 Davies HML, Du Bois J, Yu J.-Q. Chem. Soc. Rev. 2011; 40: 1855
  • 2 Crabtree RH. Chem. Rev. 2010; 110: 575
  • 3 Bergman RG. Nature (London) 2007; 446: 391
  • 4 Godula K, Sames D. Science (Washington, D. C.) 2006; 312: 67
  • 5 Labinger JA, Bercaw JE. Nature (London) 2002; 417: 507
  • 6 Doyle MP, Reactive Intermediate Chemistry. Moss RA, Platz MS, Jones Jr M. Wiley-Interscience; Hoboken, NJ 2004
    Google Scholar
  • 7 Doering WVE, Buttery RG, Laughlin RG, Chaudhuri N. J. Am. Chem. Soc. 1956; 78: 3224
  • 8 Doyle MP, Duffy R, Ratnikov M, Zhou L. Chem. Rev. 2010; 110: 704
  • 9 Davies HML, Dick AR. Top. Curr. Chem. 2010; 292: 303
  • 10 Davies HML, Manning JR. Nature (London) 2008; 451: 417
  • 11 Davies HML, Beckwith REJ. Chem. Rev. 2003; 103: 2861
  • 12 Doyle MP, Forbes DC. Chem. Rev. 1998; 98: 911
  • 13 Doyle MP. Chem. Rev. 1986; 86: 919
  • 14 Fulton JR, Aggarwal VK, de Vicente J. Eur. J. Org. Chem. 2005; 1479
  • 15 Doyle MP, van Oeveren A, Westrum LJ, Protopopova MN, Clayton Jr TW. J. Am. Chem. Soc. 1991; 113: 8982
  • 16 Doyle MP, Dyatkin AB, Roos GHP, Cañas F, Pierson DA, van Basten A, Müller P, Polleux P. J. Am. Chem. Soc. 1994; 116: 4507
  • 17 Doyle MP, Zhou Q.-L, Raab CE, Roos GHP. Tetrahedron Lett. 1995; 36: 4745
  • 18 Doyle MP, Dyatkin AB, Tedrow JS. Tetrahedron Lett. 1994; 35: 3853
  • 19 Doyle MP, Tedrow JS, Dyatkin AB, Spaans CJ, Ene DG. J. Org. Chem. 1999; 64: 8907
  • 20 Doyle MP, Kalinin AV. Synlett 1995; 1075
  • 21 Anada M, Watanabe N, Hashimoto S. Chem. Commun. (Cambridge) 1998; 1517
  • 22 Saito H, Oishi H, Kitagaki S, Nakamura S, Anada M, Hashimoto S. Org. Lett. 2002; 4: 3887
  • 23 Minami K, Saito H, Tsutsui H, Nambu H, Anada M, Hashimoto S. Adv. Synth. Catal. 2005; 347: 1483
  • 24 Takeda K, Oohara T, Anada M, Nambu H, Hashimoto S. Angew. Chem. Int. Ed. 2010; 49: 6979
  • 25 Slattery CN, Maguire AR. Org. Biomol. Chem. 2011; 9: 667
  • 26 Slattery CN, Clarke LA, OʼNeill S, Ring A, Ford A, Maguire AR. Synlett 2012; 23: 765
  • 27 Flynn CJ, Elcoate CJ, Lawrence SE, Maguire AR. J. Am. Chem. Soc. 2010; 132: 1184
  • 28 Müller P, Boléa C. Helv. Chim. Acta 2002; 85: 483
  • 29 Davies HML, Grazini MVA, Aouad E. Org. Lett. 2001; 3: 1475
  • 30 Doyle MP, Wang Y, Ghorbani P, Bappert E. Org. Lett. 2005; 7: 5035
  • 31 Takahashi T, Tsutsui H, Tamura M, Kitagaki S, Nakajima M, Hashimoto S. Chem. Commun. (Cambridge) 2001; 1604
  • 32 Watanabe N, Ohtake Y, Hashimoto S, Shiro M, Ikegami S. Tetrahedron Lett. 1995; 36: 1491
  • 33 Tsutsui H, Yamaguchi Y, Kitagaki S, Nakamura S, Anada M, Hashimoto S. Tetrahedron: Asymmetry 2003; 14: 817
  • 34 Siegel S, Schmalz HG. Angew. Chem. Int. Ed. Engl. 1997; 36: 2456
  • 35 Merlic CA, Zechman AL, Miller MM. J. Am. Chem. Soc. 2001; 123: 11101
  • 36 Davies HML, Morton D. Chem. Soc. Rev. 2011; 40: 1857
  • 37 Davies HML, Lian Y. Acc. Chem. Res. 2012; 45: 923
  • 38 Davies HML, Hansen T. J. Am. Chem. Soc. 1997; 119: 9075
  • 39 Davies HML, Hansen T, Churchill MR. J. Am. Chem. Soc. 2000; 122: 3063
  • 40 Müller P, Tohill S. Tetrahedron 2000; 56: 1725
  • 41 Ventura DL, Li Z, Coleman MG, Davies HML. Tetrahedron 2009; 65: 3052
  • 42 Davies HML, Ren P, Jin Q. Org. Lett. 2001; 3: 3587
  • 43 Davies HML, Ren P. J. Am. Chem. Soc. 2001; 123: 2070
  • 44 Davies HML, Stafford DG, Hansen T. Org. Lett. 1999; 1: 233
  • 45 Denton JR, Davies HML. Org. Lett. 2009; 11: 787
  • 46 Reddy RP, Lee GH, Davies HML. Org. Lett. 2006; 8: 3437
  • 47 Bykowski D, Wu K.-H, Doyle MP. J. Am. Chem. Soc. 2006; 128: 16038
  • 48 Suematsu H, Katsuki T. J. Am. Chem. Soc. 2009; 131: 14218
  • 49 Wang J.-C, Xu Z.-J, Guo Z, Deng Q.-H, Zhou C.-Y, Wan X.-L, Che C.-M. Chem. Commun. (Cambridge) 2012; 48: 4299
  • 50 Davies HML, Yang J. Adv. Synth. Catal. 2003; 345: 1133
  • 51 Wang P, Adams J. J. Am. Chem. Soc. 1994; 116: 3296
  • 52 Davies HML, Antoulinakis EG. Org. Lett. 2000; 2: 4153
  • 53 Davies HML, Venkataramani C, Hansen T, Hopper DW. J. Am. Chem. Soc. 2003; 125: 6462
  • 54 Davies HML, Hansen T, Hopper DW, Panaro SA. J. Am. Chem. Soc. 1999; 121: 6509
  • 55 Davies HML, Venkataramani C. Org. Lett. 2001; 3: 1773
  • 56 Axten JM, Ivy R, Krim L, Winkler JD. J. Am. Chem. Soc. 1999; 121: 6511
  • 57 Davies HML, Jin Q, Ren P, Kovalevsky AYu. J. Org. Chem. 2002; 67: 4165
  • 58 Davies HML, Hedley SJ, Bohall BR. J. Org. Chem. 2005; 70: 10737
  • 59 Nadeau E, Li Z, Morton D, Davies HML. Synlett 2009; 151
  • 60 Thu H.-Y, Tong GS.-M, Huang J.-S, Chan SL.-F, Deng Q.-H, Che C.-M. Angew. Chem. Int. Ed. 2008; 47: 9747
  • 61 Davies HML, Venkataramani C. Angew. Chem. Int. Ed. 2002; 41: 2197
  • 62 Davies HML, Jin Q. Org. Lett. 2004; 6: 1769
  • 63 Davies HML, Ni A. Chem. Commun. (Cambridge) 2006; 3110
  • 64 DeAngelis A, Shurtleff VW, Dmitrenko O, Fox JM. J. Am. Chem. Soc. 2011; 133: 1650
  • 65 Boruta DT, Dmitrenko O, Yap GPA, Fox JM. Chem. Sci. 2012; 3: 1589
  • 66 Mbuvi HM, Woo LK. Organometallics 2008; 27: 637
  • 67 Cai Y, Zhu S.-F, Wang G.-P, Zhou Q.-L. Adv. Synth. Catal. 2011; 353: 2939
  • 68 Slattery CN, Ford A, Maguire AR. Tetrahedron 2010; 66: 6681
  • 69 Doyle MP, Protopopova MN, Winchester WR, Daniel KL. Tetrahedron Lett. 1992; 33: 7819