메뉴 건너뛰기




Volumn 48, Issue 28, 2009, Pages 5094-5115

Palladium(II)-cataIyzed C-H aetivation/C-C cross-coupling reactions: Versatility and practicality

Author keywords

C C coupling; C H activation; Organometallic reagent; Palladium

Indexed keywords

ALKYL HALIDES; BOND-FORMING REACTIONS; C-C BONDS; C-C COUPLING; C-H ACTIVATION; C-H BOND; CATALYTIC CYCLES; CATALYTIC TRANSFORMATION; CATALYZED COUPLING; CROSS COUPLING REACTIONS; ORGANOMETALLIC REAGENT; STATE OF THE ART;

EID: 67649488045     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200806273     Document Type: Review
Times cited : (3793)

References (282)
  • 1
    • 70349945490 scopus 로고    scopus 로고
    • For reviews, see
    • For reviews, see:
  • 4
    • 0000633011 scopus 로고
    • Eds, B.M. Trost, I. Fleming, Pergamon, Oxford
    • b) R. F. Heck in Comprehensive Organic Synthesis, Vol.4 (Eds.: B.M. Trost, I. Fleming), Pergamon, Oxford, 1991, p. 833;
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 833
    • Heck, R.F.1
  • 6
    • 0003748614 scopus 로고    scopus 로고
    • Eds, F. Diederich, P. J. Stang, Wiley-VCH, New York
    • d) Metal-Catalyzed CrossCoupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, New York, 1998;
    • (1998) Metal-Catalyzed CrossCoupling Reactions
  • 10
    • 0042379988 scopus 로고    scopus 로고
    • B. M. Trost, M. L. Crawley, Chem. Rev. 2003, 103, 2921;
    • h) B. M. Trost, M. L. Crawley, Chem. Rev. 2003, 103, 2921;
  • 11
    • 70349919399 scopus 로고    scopus 로고
    • K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem. 2005, 111, 4516; Angew. Chem. Int. Ed. 2005, 44, 4442;
    • i) K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem. 2005, 111, 4516; Angew. Chem. Int. Ed. 2005, 44, 4442;
  • 12
    • 70349909139 scopus 로고    scopus 로고
    • D. S. Surry, S. L. Buchwald, Angew. Chem. 2008, 120, 6438; Angew. Chem. Int. Ed, 2008, 47, 6338;
    • j) D. S. Surry, S. L. Buchwald, Angew. Chem. 2008, 120, 6438; Angew. Chem. Int. Ed, 2008, 47, 6338;
  • 13
    • 52149114261 scopus 로고    scopus 로고
    • J. F. Hartwig, Nature 2008, 455, 314; 1 S. E. Denmark, C. S. Regens, Ace. Chem. Res. 2008, 41, 1486.
    • k) J. F. Hartwig, Nature 2008, 455, 314; 1) S. E. Denmark, C. S. Regens, Ace. Chem. Res. 2008, 41, 1486.
  • 14
    • 70349958653 scopus 로고    scopus 로고
    • For ligand developments, see
    • For ligand developments, see:
  • 22
    • 70349938438 scopus 로고    scopus 로고
    • For reviews on C-H activation chemistry, see
    • For reviews on C-H activation chemistry, see :
  • 27
  • 29
    • 70349960433 scopus 로고    scopus 로고
    • For comprehensive reviews on cyclopalladation reactions, see
    • For comprehensive reviews on cyclopalladation reactions, see :
  • 32
    • 0039972967 scopus 로고    scopus 로고
    • 2 C-H bonds directed by azo groups, see: A. C Cope, R. W. Siekman, J. Am. Chem. Soc. 1965, 87, 3272;
    • 2 C-H bonds directed by azo groups, see: A. C Cope, R. W. Siekman, J. Am. Chem. Soc. 1965, 87, 3272;
  • 33
    • 9244238546 scopus 로고    scopus 로고
    • 3)-H bonds directed by oximes see: A. G. Constable, W S. McDonald, L. C. Sawkins, B. L. Shaw, J. Chem. Soc. Chem. Commun. 1978, 1061.
    • 3)-H bonds directed by oximes see: A. G. Constable, W S. McDonald, L. C. Sawkins, B. L. Shaw, J. Chem. Soc. Chem. Commun. 1978, 1061.
  • 34
    • 70349966632 scopus 로고    scopus 로고
    • For early examples of exploiting cyclopalladation reactions in synthesis, see
    • For early examples of exploiting cyclopalladation reactions in synthesis, see:
  • 38
    • 70349960442 scopus 로고    scopus 로고
    • For development of mechanistic models of cyclopalladation reactions, see
    • For development of mechanistic models of cyclopalladation reactions, see:
  • 89
    • 70349947780 scopus 로고    scopus 로고
    • For early proposal of formation of platinum(IV) complexes, see: W. J. Pope, S. J. Peachy, Proc. Chem. Soc. London 1907, 23, 86;
    • a) For early proposal of formation of platinum(IV) complexes, see: W. J. Pope, S. J. Peachy, Proc. Chem. Soc. London 1907, 23, 86;
  • 90
    • 0037100447 scopus 로고    scopus 로고
    • 2, see: V. V. Rostovtsev, L. M. Henling, J. A. Labinger, J. E. Bercaw, Inorg. Chem 2002, 41, 3608.
    • 2, see: V. V. Rostovtsev, L. M. Henling, J. A. Labinger, J. E. Bercaw, Inorg. Chem 2002, 41, 3608.
  • 101
    • 70349951072 scopus 로고    scopus 로고
    • R. Giri, J. Chen, J.-Q. Yu, Angew. Chem. 2005, 117, 2150; Angew. Chem. Int. Ed. 2005, 44, 2112;
    • a) R. Giri, J. Chen, J.-Q. Yu, Angew. Chem. 2005, 117, 2150; Angew. Chem. Int. Ed. 2005, 44, 2112;
  • 102
    • 70349960439 scopus 로고    scopus 로고
    • R. Giri, J. Liang, J.-G. Lei, J.-J. Li, D-H. Wang, J. Chen, I. C. Naggar, C. Guo, B. M. Foxman, J.-Q. Yu, Angew. Chem. 2005, 117, 7586; Angew. Chem. Int. Ed. 2005, 44, 7420.
    • b) R. Giri, J. Liang, J.-G. Lei, J.-J. Li, D-H. Wang, J. Chen, I. C. Naggar, C. Guo, B. M. Foxman, J.-Q. Yu, Angew. Chem. 2005, 117, 7586; Angew. Chem. Int. Ed. 2005, 44, 7420.
  • 103
    • 70349947779 scopus 로고    scopus 로고
    • IV catalysis, see:
    • IV catalysis, see:
  • 111
    • 25444458063 scopus 로고    scopus 로고
    • V. G. Zaitsev, D. Shabashov, O. Daugulis, J. Am. Chem. Soc. 2005, 127, 13154;
    • a) V. G. Zaitsev, D. Shabashov, O. Daugulis, J. Am. Chem. Soc. 2005, 127, 13154;
  • 127
    • 70349956961 scopus 로고    scopus 로고
    • For recent arylation of heterocycles with aryltosylates and aryltriflates, see
    • For recent arylation of heterocycles with aryltosylates and aryltriflates, see:
  • 128
    • 70349963412 scopus 로고    scopus 로고
    • L. Ackermann, A. Althammer, S. Fenner, Angew. Chem 2009, 127, 207; Angew. Chem Int. Ed 2009, 48, 201;
    • a) L. Ackermann, A. Althammer, S. Fenner, Angew. Chem 2009, 127, 207; Angew. Chem Int. Ed 2009, 48, 201;
  • 146
    • 34547883488 scopus 로고    scopus 로고
    • H. A. Chiong, Q.-N. Pham, O. Daugulis, J. Am. Chem. Soc. 2007, 129, 9879.
    • c) H. A. Chiong, Q.-N. Pham, O. Daugulis, J. Am. Chem. Soc. 2007, 129, 9879.
  • 149
    • 0001468409 scopus 로고    scopus 로고
    • G. Dyker, J. Org. Chem. 1993, 58, 6426;
    • b) G. Dyker, J. Org. Chem. 1993, 58, 6426;
  • 150
    • 0010821235 scopus 로고
    • c) G. Dyker, Chem. Ber. 1994, 127, 739;
    • (1994) Chem. Ber , vol.127 , pp. 739
    • Dyker, G.1
  • 166
    • 0037059546 scopus 로고    scopus 로고
    • J.-Y. Cho, M. K. Tse, D. Holmes, R. E. Maleczka Jr. , M. R. Smith III, Science 2002, 295, 305;
    • d) J.-Y. Cho, M. K. Tse, D. Holmes, R. E. Maleczka Jr. , M. R. Smith III, Science 2002, 295, 305;
  • 168
    • 0038788823 scopus 로고    scopus 로고
    • A. D. Sadow, T. D. Tilley, J. Am. Chem. Soc. 2003, 125, 7971;
    • f) A. D. Sadow, T. D. Tilley, J. Am. Chem. Soc. 2003, 125, 7971;
  • 176
    • 34250851338 scopus 로고    scopus 로고
    • B. X Stokes, H. Dong, B. E. Leslie, A. L. Pumphrey, TG. Driver, J. Am. Chem. Soc. 2007, 129, 7500;
    • m) B. X Stokes, H. Dong, B. E. Leslie, A. L. Pumphrey, TG. Driver, J. Am. Chem. Soc. 2007, 129, 7500;
  • 179
    • 70349940087 scopus 로고    scopus 로고
    • For recent development of copper-catalyzed C-H functionalizations, see
    • For recent development of copper-catalyzed C-H functionalizations, see :
  • 187
    • 46049110936 scopus 로고    scopus 로고
    • R. J. Phipps, N. P. Grimster, M. J. Gaunt, J. Am. Chem. Soc. 2008, 130, 8172;
    • f) R. J. Phipps, N. P. Grimster, M. J. Gaunt, J. Am. Chem. Soc. 2008, 130, 8172;
  • 190
    • 35348876788 scopus 로고    scopus 로고
    • For recent development of iron-catalyzed C-H functionalizations, see: a
    • For recent development of iron-catalyzed C-H functionalizations, see: a) Y. Zhang, C.-J. Li, Eur. J. Org. Chem. 2007, 4654;
    • (2007) Eur. J. Org. Chem , pp. 4654
    • Zhang, Y.1    Li, C.-J.2
  • 195
    • 0037442914 scopus 로고    scopus 로고
    • F. Kakiuchi, S. Kan, K. Igi, N Chatani, S. Murai, J. Am. Chem. Soc. 2003, 125,1698;
    • b) F. Kakiuchi, S. Kan, K. Igi, N Chatani, S. Murai, J. Am. Chem. Soc. 2003, 125,1698;
  • 200
    • 17444373318 scopus 로고    scopus 로고
    • For a review on the mechanisms of the Stille reaction, see
    • For a review on the mechanisms of the Stille reaction, see: P. Espinet, A. M. Echavarren, Angew. Chem. 2004, 116, 4808;
    • (2004) Angew. Chem , vol.116 , pp. 4808
    • Espinet, P.1    Echavarren, A.M.2
  • 204
    • 0344012068 scopus 로고    scopus 로고
    • R. C. Verboom, B. J. Plietker, J.-E. Bäckvall, J. Organomet. Chem. 2003, 687, 508;
    • b) R. C. Verboom, B. J. Plietker, J.-E. Bäckvall, J. Organomet. Chem. 2003, 687, 508;
  • 211
    • 54849420705 scopus 로고    scopus 로고
    • For detailed discussion and evidence for cation-promoted palladium insertion into C-H bonds, see
    • For detailed discussion and evidence for cation-promoted palladium insertion into C-H bonds, see: R. Giri, J.-Q. Yu, J. Am Chem. Soc. 2008, 130, 14082.
    • (2008) J. Am Chem. Soc , vol.130 , pp. 14082
    • Giri, R.1    Yu, J.-Q.2
  • 216
    • 33751155775 scopus 로고    scopus 로고
    • 3K, see: a E. Vedejs, R. W. Chapman, S. C. Fields, S. Lin, M. R. Schrimpf, J. Org. Chem. 1995, 60, 3020;
    • 3K, see: a) E. Vedejs, R. W. Chapman, S. C. Fields, S. Lin, M. R. Schrimpf, J. Org. Chem. 1995, 60, 3020;
  • 220
    • 41149138082 scopus 로고    scopus 로고
    • H. Ge, M. J. Niphakis, G. I. Georg, J. Am Chem. Soc. 2008, 130, 3708;
    • a) H. Ge, M. J. Niphakis, G. I. Georg, J. Am Chem. Soc. 2008, 130, 3708;
  • 228
    • 70349951065 scopus 로고    scopus 로고
    • J.. Li, J. Yang, M. C. Kozlowski, Org. Lett. 2001, 5, 1137.
    • d) J.. Li, J. Yang, M. C. Kozlowski, Org. Lett. 2001, 5, 1137.
  • 238
    • 34848899222 scopus 로고    scopus 로고
    • K. L. Hull, M. S. Sanford,J. Am, Chem. Soc. 2007, 129, 11904;
    • a) K. L. Hull, M. S. Sanford,J. Am, Chem. Soc. 2007, 129, 11904;
  • 240
    • 70349955370 scopus 로고    scopus 로고
    • B.-J.. Li, S.-L. Tian, Z. Fang, Z.-J. Shi, Angew. Chem. 2008, 120, 1131;
    • c) B.-J.. Li, S.-L. Tian, Z. Fang, Z.-J. Shi, Angew. Chem. 2008, 120, 1131;
  • 242
    • 70349968694 scopus 로고    scopus 로고
    • M. R. Netherton, C Dai, K. Neuschütz, G. C Fu, J. Am. Chem. Soc. 2001, 125, 10099;
    • a) M. R. Netherton, C Dai, K. Neuschütz, G. C Fu, J. Am. Chem. Soc. 2001, 125, 10099;
  • 247
    • 0003445429 scopus 로고    scopus 로고
    • Eds, E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Springer, New York
    • Comprehensive Asymmetric Catalysis (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, New York, 1999.
    • (1999) Comprehensive Asymmetric Catalysis
  • 248
    • 70349936815 scopus 로고    scopus 로고
    • 3)-H bonds, see: M. C. Whisler, S. MacNeil, V Snieckus, P. Beak, Angew. Chem. 2004, 116, 2256;
    • 3)-H bonds, see: M. C. Whisler, S. MacNeil, V Snieckus, P. Beak, Angew. Chem. 2004, 116, 2256;
  • 260
    • 70349952917 scopus 로고    scopus 로고
    • For reviews on enantioselective C-H activation by carbene and nitrene insertions, see
    • For reviews on enantioselective C-H activation by carbene and nitrene insertions, see:
  • 262
    • 33845532561 scopus 로고    scopus 로고
    • M.P. Doyle, J. Org. Chem. 2006, 71, 9253;
    • b)M.P. Doyle, J. Org. Chem. 2006, 71, 9253;
  • 266
  • 267
    • 0033473876 scopus 로고    scopus 로고
    • For elegant approaches of combining C-H activation and asymmetric hydrorhodation or carbopalladation, see: a K. Mikami, M. Hatano, M. Terada, Chem. Lett. 1999, 55;
    • For elegant approaches of combining C-H activation and asymmetric hydrorhodation or carbopalladation, see: a) K. Mikami, M. Hatano, M. Terada, Chem. Lett. 1999, 55;
  • 268
    • 2942528733 scopus 로고    scopus 로고
    • b R. K. Thalji, J. A. Ellman, R. G. Bergman, J. Am. Chem. Soc. 2004, 126, 7192.
    • b) R. K. Thalji, J. A. Ellman, R. G. Bergman, J. Am. Chem. Soc. 2004, 126, 7192.
  • 269
    • 70349942782 scopus 로고    scopus 로고
    • For palladium-catalyzed asymmetric allylic C-H oxidation, see
    • For palladium-catalyzed asymmetric allylic C-H oxidation, see:
  • 275
    • 70349949485 scopus 로고    scopus 로고
    • For a review on copper(I)-catalyzed asymmetric KharaschSosnovsky reaction, see: X Eames, M. Watkinson, Angew. Chem. 2001, 113, 3679;
    • For a review on copper(I)-catalyzed asymmetric KharaschSosnovsky reaction, see: X Eames, M. Watkinson, Angew. Chem. 2001, 113, 3679;
  • 277
    • 70349956954 scopus 로고    scopus 로고
    • R-F. Shi, N. Maugel, Y-H. Zhang, J.-Q. Yu, Angew. Chem. 2008, 120, 4960; Angew. Chem. Int. Ed. 2008, 47,4882.
    • R-F. Shi, N. Maugel, Y-H. Zhang, J.-Q. Yu, Angew. Chem. 2008, 120, 4960; Angew. Chem. Int. Ed. 2008, 47,4882.
  • 278
    • 0037467414 scopus 로고    scopus 로고
    • D. A. Evans, F. E. Michael, J. S. Tedrow, K. R. Campos, J. Am. Chem. Soc. 2003, 125, 3534.
    • D. A. Evans, F. E. Michael, J. S. Tedrow, K. R. Campos, J. Am. Chem. Soc. 2003, 125, 3534.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.