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Yu, J.-Q.: 2016 Science of Synthesis, 3a: Catalytic Transformations via C—H Activation 1 DOI: 10.1055/sos-SD-217-00115
Catalytic Transformations via C—H Activation 1

1.1.7 Metal-Catalyzed C—H Alkylation Using RX Compounds

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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 1

Subtitle: C-C, C-N, C-O, C-Hal, and C-B Bond Formation

Print ISBN: 9783131711311; Online ISBN: 9783132403413; Book DOI: 10.1055/b-003-129295

1st edition © 2016 Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

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

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Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Type: Multivolume Edition

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Abstract

This review covers transition-metal-catalyzed C(sp2)—H alkylation methods via carbon—heteroatom bond cleavage. The first part of the review delineates catalytic C(sp2)—H alkylation methods for arene and alkene substrates using various alkyl halides. Subsequently, alkylation by cleavage of C—B, C—Si, and C—Sn bonds is described. Finally, C(sp2)—H alkylation via C—O and C—S bond cleavage is reviewed.

Key words

alkylation - C—H activation - arenes - alkenes - transition-metal catalysts
 
  • 1 Roberts RM, Khalaf AA. Friedel–Crafts Alkylation Chemistry: A Century of Discovery. Dekker; New York 1984
    Google Scholar
  • 2 Olah GA, Krishnamurti R, Prakash GKS, Comprehensive Organic Synthesis. Trost BM, Fleming I. Pergamon; Oxford 1991. 3.
    Google Scholar
  • 3 Heck RF. Acc. Chem. Res. 1979; 12: 146
  • 4 Nicolaou KC, Bulger PG, Sarlah D. Angew. Chem. Int. Ed. 2005; 44: 4442
    PubMed
  • 5 Zakzeski J, Bruijnincx PCA, Jongerius AL, Weckhuysen BM. Chem. Rev. 2010; 110: 3552
    PubMed
  • 6 van Putten R.-J, van der Waal JC, de Jong E, Rasrendra CB, Heeres HJ, de Vries JG. Chem. Rev. 2013; 113: 1499
    PubMed
  • 7 Jia C, Kitamura T, Fujiwara Y. Acc. Chem. Res. 2001; 34: 633
    PubMed
  • 8 Ritleng V, Sirlin C, Pfeffer M. Chem. Rev. 2002; 102: 1731
    PubMed
  • 9 Colby DA, Bergman RG, Ellman JA. Chem. Rev. 2010; 110: 624
    PubMed
  • 10 Murai S, Kakiuchi F, Sekine S, Tanaka Y, Kamatani A, Sonoda M, Chatani N. Nature (London) 1993; 366: 529
  • 11 Kakiuchi F, Murai S. Acc. Chem. Res. 2002; 35: 826
    PubMed
  • 12 Kakiuchi F. Top. Organomet. Chem. 2007; 24: 1
  • 13 Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147
    PubMed
  • 14 Daugulis O, Do H.-Q, Shabashov D. Acc. Chem. Res. 2009; 42: 1074
    PubMed
  • 15 Li C.-J. Acc. Chem. Res. 2009; 42: 335
    PubMed
  • 16 Sun C.-L, Li B.-J, Shi Z.-J. Chem. Commun. (Cambridge) 2010; 46: 677
    PubMed
  • 17 Yeung CS, Dong VM. Chem. Rev. 2011; 111: 1215
    PubMed
  • 18 Yamaguchi J, Yamaguchi AD, Itami K. Angew. Chem. Int. Ed. 2012; 51: 8960
    PubMed
  • 19 Ackermann L, Novák P, Vicente R, Hofmann N. Angew. Chem. Int. Ed. 2009; 48: 6045
    PubMed
  • 20 Ackermann L, Novák P. Org. Lett. 2009; 11: 4966
    PubMed
  • 21 Ackermann L, Hofmann N, Vicente R. Org. Lett. 2011; 13: 1875
    PubMed
  • 22 Zhao Y, Chen G. Org. Lett. 2011; 13: 4850
    PubMed
  • 23 Aihara Y, Chatani N. J. Am. Chem. Soc. 2013; 135: 5308
    PubMed
  • 24 Chen Q, Ilies L, Nakamura E. J. Am. Chem. Soc. 2011; 133: 428
    PubMed
  • 25 Li B, Wu Z.-H, Gu Y.-F, Sun C.-L, Wang B.-Q, Shi Z.-J. Angew. Chem. Int. Ed. 2011; 50: 1109
    PubMed
  • 26 Mariampillai B, Alberico D, Bidau V, Lautens M. J. Am. Chem. Soc. 2006; 128: 14436
    PubMed
  • 27 Mariampillai B, Alliot J, Li M, Lautens M. J. Am. Chem. Soc. 2007; 129: 15372
    PubMed
  • 28 Catellani M, Frignani F, Rangoni A. Angew. Chem. Int. Ed. 1997; 36: 119
  • 29 Bressy C, Alberico D, Lautens M. J. Am. Chem. Soc. 2005; 127: 13148
    PubMed
  • 30 Laleu B, Lautens M. J. Org. Chem. 2008; 73: 9164
    PubMed
  • 31 Martins A, Lautens M. J. Org. Chem. 2008; 73: 8705
    PubMed
  • 32 Weinstabl H, Suhartono M, Qureshi Z, Lautens M. Angew. Chem. Int. Ed. 2013; 52: 5305
    PubMed
  • 33 Hofmann N, Ackermann L. J. Am. Chem. Soc. 2013; 135: 5877
    PubMed
  • 34 Zhang Y.-H, Shi B.-F, Yu J.-Q. Angew. Chem. Int. Ed. 2009; 48: 6097
    PubMed
  • 35 Beaulieu L.-PB, Roman DS, Vallée F, Charette AB. Chem. Commun. (Cambridge) 2012; 48: 8249
    PubMed
  • 36 Chen X, Goodhue CE, Yu J.-Q. J. Am. Chem. Soc. 2006; 128: 12634
    PubMed
  • 37 Chu J.-H, Chen C.-C, Wu M.-J. Organometallics 2008; 27: 5173
  • 38 Giri R, Maugel N, Li J.-J, Wang D.-H, Breazzano SP, Saunders LB, Yu J.-Q. J. Am. Chem. Soc. 2007; 129: 3510
    PubMed
  • 39 Thuy-Boun PS, Villa G, Dang D, Richardson P, Su S, Yu J.-Q. J. Am. Chem. Soc. 2013; 135: 17508
    PubMed
  • 40 Rosen BR, Simke LR, Thuy-Boun PS, Dixon DD, Yu J.-Q, Baran PS. Angew. Chem. Int. Ed. 2013; 52: 7317
    PubMed
  • 41 Engle KM, Wang D.-H, Yu J.-Q. J. Am. Chem. Soc. 2010; 132: 14137
    PubMed
  • 42 Lu Y, Wang D.-H, Engle KM, Yu J.-Q. J. Am. Chem. Soc. 2010; 132: 5916
    PubMed
  • 43 Engle KM, Thuy-Boun PS, Dang M, Yu J.-Q. J. Am. Chem. Soc. 2011; 133: 18183
    PubMed
  • 44 Chen X, Li J.-J, Hao X.-S, Goodhue CE, Yu J.-Q. J. Am. Chem. Soc. 2006; 128: 78
    PubMed
  • 45 Neufeldt SR, Seigerman CK, Sanford MS. Org. Lett. 2013; 15: 2302
    PubMed
  • 46 Robbins DW, Hartwig JF. Angew. Chem. Int. Ed. 2013; 52: 933
    PubMed
  • 47 Chu L, Qing F.-L. J. Am. Chem. Soc. 2012; 134: 1298
    PubMed
  • 48 Ye Y, Lee SH, Sanford MS. Org. Lett. 2011; 13: 5464
    PubMed
  • 49 Smith MB, March J. Marchʼs Advanced Organic Chemistry. Wiley; New York 2001
    Google Scholar
  • 50 Whitney S, Grigg R, Derrick A, Keep A. Org. Lett. 2007; 9: 3299
    PubMed
  • 51 Wong CM, Vuong KQ, Gatus MRD, Hua C, Bhadbhade M, Messerle BA. Organometallics 2012; 31: 7500
  • 52 Lee D.-H, Kwon K.-H, Yi CS. Science (Washington, D. C.) 2011; 333: 1613
    PubMed
  • 53 Lee D.-H, Kwon K.-H, Yi CS. J. Am. Chem. Soc. 2012; 134: 7325
    PubMed
  • 54 Blank B, Kempe R. J. Am. Chem. Soc. 2010; 132: 924
    PubMed
  • 55 Obora Y, Ogawa S, Yamamoto N. J. Org. Chem. 2012; 77: 9429
    PubMed
  • 56 Mukai T, Hirano K, Satoh T, Miura M. Org. Lett. 2010; 12: 1360
    PubMed
  • 57 Wang X, Truesdale L, Yu J.-Q. J. Am. Chem. Soc. 2010; 132: 3648
    PubMed
  • 58 Zhang X.-G, Dai H.-X, Wasa M, Yu J.-Q. J. Am. Chem. Soc. 2012; 134: 11948
    PubMed