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Volumn 66, Issue 27-28, 2010, Pages 5283-5294

Copper-catalyzed cross-coupling of amides and potassium alkenyltrifluoroborate salts: A general approach to the synthesis of enamides

Author keywords

Copper catalysis; Enamide synthesis; Organoboron compounds; Organotrifluoroborate salt; Oxidative cross coupling reaction

Indexed keywords

ACETAL DERIVATIVE; ACETAMIDE DERIVATIVE; ALKENE; ALPHA BETA UNSATURATED CARBONYL; AMIDE; BENZAMIDE DERIVATIVE; BORONIC ACID DERIVATIVE; CARBAMIC ACID DERIVATIVE; CARBONYL DERIVATIVE; COPPER; DICHLOROMETHANE; DIMETHYL SULFOXIDE; HALIDE; IMIDE; POTASSIUM ALKENYLTRIFLUOROBORATE SALT; SODIUM CHLORIDE; UNCLASSIFIED DRUG;

EID: 77954348540     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.03.076     Document Type: Article
Times cited : (35)

References (139)
  • 9
    • 0345134728 scopus 로고    scopus 로고
    • For reviews, see
    • For reviews, see: (a) Yet, L. Chem. Rev. 2003,103,4283-4306
    • (2003) Chem. Rev. , vol.103 , pp. 4283-4306
    • Yet, L.1
  • 12
    • 0034605899 scopus 로고    scopus 로고
    • For selected references of total syntheses of enamide natural products
    • For selected references of total syntheses of enamide natural products, see: (a) Wu, Y. S.; Esser, L.; De Brabander,J. K. Angew. Chem., Int. Ed. 2000,39,4308-4310
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 4308-4310
    • Wu, Y.S.1    Esser, L.2    De Brabander, J.K.3
  • 15
    • 0037613530 scopus 로고    scopus 로고
    • (d) Wang, X.; Porco, J. A., Jr.J. Am. Chem. Soc. 2003,125,6040-6041
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 6040-6041
    • Wang, X.1
  • 44
    • 38349170142 scopus 로고    scopus 로고
    • Re-catalyzed amidation of alkynes
    • Re-catalyzed amidation of alkynes: Yudha, S.; Kuninobu, S. Y.; Takai, K. Org. Lett. 2007, 9, 5609-5611.
    • (2007) Org. Lett. , vol.9 , pp. 5609-5611
    • Yudha, S.1    Kuninobu, S.Y.2    Takai, K.3
  • 45
    • 55949122495 scopus 로고    scopus 로고
    • Ni-catalyzed multicomponent coupling of ynamides, aldehydes, and silane
    • Ni-catalyzed multicomponent coupling of ynamides, aldehydes, and silane: Saito, N.; Katayama, T.; Sato, Y. Org. Lett. 2008, 10, 3829-3832.
    • (2008) Org. Lett. , vol.10 , pp. 3829-3832
    • Saito, N.1    Katayama, T.2    Sato, Y.3
  • 46
    • 33847087023 scopus 로고
    • Fe and Rh-catalyzed isomerization of N-allylamides
    • Fe and Rh-catalyzed isomerization of N-allylamides: (a) Stille, J. K.; Becker, Y. J. Org. Chem. 1980, 45, 2139-2145
    • (1980) J. Org. Chem. , vol.45 , pp. 2139-2145
    • Stille, J.K.1    Becker, Y.2
  • 49
    • 61449084647 scopus 로고    scopus 로고
    • Rh-catalyzed hydroacylation of ketoximes
    • Rh-catalyzed carbozincation and hy-drozincation of ynamides
    • Rh-catalyzed hydroacylation of ketoximes: (a) Guan, Z.-H.; Huang, K.; Yu, S.; Zhang, X. Org. Lett. 2009, 11, 481-483; Rh-catalyzed carbozincation and hy-drozincation of ynamides
    • (2009) Org. Lett. , vol.11 , pp. 481-483
    • Guan, Z.-H.1    Huang, K.2    Yu, S.3    Zhang, X.4    Gourdet, B.5    Lam, H.W.6
  • 51
    • 0036134301 scopus 로고    scopus 로고
    • Pd-catalyzed intramolecular coupling between amides and alkenyl halides Pd-catalyzed oxidative amidation of conjugated olefins
    • Pd-catalyzed intramolecular coupling between amides and alkenyl halides: (a) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002,43,111-114; Pd-catalyzed oxidative amidation of conjugated olefins:
    • (2002) Tetrahedron Lett. , vol.43 , pp. 111-114
    • Kozawa, Y.1    Mori, M.2
  • 53
    • 8544242698 scopus 로고    scopus 로고
    • Pd-catalyzed coupling between amides, and enol ethers
    • (c) Harrison, P.; Meek, G. Tetrahedron Lett. 2004, 45, 9277-9280; Pd-catalyzed coupling between amides, and enol ethers
    • (2004) Tetrahedron Lett. , vol.45 , pp. 9277-9280
    • Harrison, P.1    Meek, G.2
  • 61
  • 63
    • 0036589259 scopus 로고    scopus 로고
    • In recent years, there has been an increased interest in copper-catalyzed transformations. For recent reviews
    • In recent years, there has been an increased interest in copper-catalyzed transformations. For recent reviews, see: (a) Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359-1469
    • (2002) Chem. Rev. , vol.102 , pp. 1359-1469
    • Hassan, J.1    Sevignon, M.2    Gozzi, C.3    Schulz, E.4    Lemaire, M.5
  • 78
    • 19544380068 scopus 로고    scopus 로고
    • (h) Hu, T.; Li, C. Org. Lett. 2005, 7,2035-2038
    • (2005) Org. Lett. , vol.7 , pp. 2035-2038
    • Hu, T.1    Li, C.2
  • 84
    • 33644647605 scopus 로고    scopus 로고
    • Hall, D. G., Ed.; Wiley-VCH: Weinheim
    • Chan, D. M. T.; Lam, P. Y. S. In Boronic Acids; Hall, D. G., Ed.; Wiley-VCH: Weinheim, 2005; pp 205-240.
    • (2005) Boronic Acids , pp. 205-240
    • Chan, D.M.T.1    Lam, P.Y.S.2
  • 100
    • 0000141045 scopus 로고    scopus 로고
    • For examples of leading references for Rh-catalyzed additions to aldehydes and ketones
    • For examples of leading references for Rh-catalyzed additions to aldehydes and ketones, see: (a) Batey, R. A.; Thadani, A. N.; Smil, D. V. Org. Lett. 1999,1,1683-1686
    • (1999) Org. Lett. , vol.1 , pp. 1683-1686
    • Batey, R.A.1    Thadani, A.N.2    Smil, D.V.3
  • 102
    • 0036845262 scopus 로고    scopus 로고
    • For examples of leading references for Rh or Pd-catalyzed additions of orga-notrifluoroborate salts to enones
    • For examples of leading references for Rh or Pd-catalyzed additions of orga-notrifluoroborate salts to enones, see: Ref. 37a and: (a) Pucheault, M.; Darses, S.; Genet, J.-P. Eur. J. Org. Chem. 2002,21, 3552-3557
    • (2002) Eur. J. Org. Chem. , vol.21 , pp. 3552-3557
    • Pucheault, M.1    Darses, S.2    Genet, J.-P.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.