메뉴 건너뛰기




Volumn 351, Issue 6, 2009, Pages 855-858

Copper-Catalyzed conjugate addition of diboron reagents to α,β-unsaturated amides: Highly reactive copper-1,2- bis(diphenylphosphino)benzene catalyst system

Author keywords

Amides; Boron; Conjugate addition; Copper; Ligand effects; Phosphine ligands

Indexed keywords


EID: 65349163741     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200900040     Document Type: Article
Times cited : (132)

References (41)
  • 1
    • 0002253853 scopus 로고    scopus 로고
    • Platinum: a Y. G. Lawson, M. J. G. Lesley, T. B. Marder, N. C. Norman, C. R. Rice, Chem. Commun. 1997, 2051-2052;
    • Platinum: a) Y. G. Lawson, M. J. G. Lesley, T. B. Marder, N. C. Norman, C. R. Rice, Chem. Commun. 1997, 2051-2052;
  • 6
    • 0006272242 scopus 로고    scopus 로고
    • K. Takahashi, T. Ishiyama, N. Miyaura, J. Organomet. Chem. 2001, 625, 47-53; nickel:
    • f) K. Takahashi, T. Ishiyama, N. Miyaura, J. Organomet. Chem. 2001, 625, 47-53; nickel:
  • 10
    • 37549021866 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 145-147.
    • (2008) Angew. Chem. Int. Ed , vol.47 , pp. 145-147
  • 15
    • 2942752129 scopus 로고    scopus 로고
    • For examples of copper-catalyzed conjugate additions to protected amides, such as imides, carbamates, oxazo-lidinones, see: a M. Pineschi, F. Del Moro, F. Gini, A. J. Minnaard, B. L. Feringa, Chem. Commun. 2004, 1244-1245;
    • For examples of copper-catalyzed conjugate additions to protected amides, such as imides, carbamates, oxazo-lidinones, see: a) M. Pineschi, F. Del Moro, F. Gini, A. J. Minnaard, B. L. Feringa, Chem. Commun. 2004, 1244-1245;
  • 17
    • 48849085472 scopus 로고    scopus 로고
    • One preparation example of organotrifluoroborate salt from dimethyl acrylamide via two steps by using our copper-catalyzed method as the first step was reported, but the efficiency of the step was not reported; G. A. Molander, D. E. Petrillo, Org. Lett. 2008, 10, 1795-1798.
    • One preparation example of organotrifluoroborate salt from dimethyl acrylamide via two steps by using our copper-catalyzed method as the first step was reported, but the efficiency of the step was not reported; G. A. Molander, D. E. Petrillo, Org. Lett. 2008, 10, 1795-1798.
  • 19
    • 65349155661 scopus 로고    scopus 로고
    • Xantphos, 9,9-dimethyl-4,5-bis(diphenylphosphino)-xanthene
    • Xantphos = 9,9-dimethyl-4,5-bis(diphenylphosphino)-xanthene.
  • 23
    • 60749120309 scopus 로고    scopus 로고
    • In our study on the asymmetric β-boration of acyclic enones, we found that a rigid and strong coordination between ligand and catalyst would be needed for high enantioselectivity. Therefore, we excluded P,N- and N,N-type ligands and monophosphine ligands for future application of this current study on the asymmetric synthesis of β-borylamides: H.-S. Sim, X. Feng, J. Yun, Chem. Eur. J. 2009, 15, 1939-1943
    • In our study on the asymmetric β-boration of acyclic enones, we found that a rigid and strong coordination between ligand and catalyst would be needed for high enantioselectivity. Therefore, we excluded P,N- and N,N-type ligands and monophosphine ligands for future application of this current study on the asymmetric synthesis of β-borylamides: H.-S. Sim, X. Feng, J. Yun, Chem. Eur. J. 2009, 15, 1939-1943.
  • 24
    • 85153017909 scopus 로고    scopus 로고
    • For a series of copper(I) halide complexes [(P - P)CuX - S] with a chelating phosphine (P - P) and heterocyclic thiones, see: a) P. Aslanidis, P. J. Cox, A. Kaltzoglou, A. C. Tsipis, Eur. J. Inorg. Chem. 2006, 334-344;
    • For a series of copper(I) halide complexes [(P - P)CuX - S] with a chelating phosphine (P - P) and heterocyclic thiones, see: a) P. Aslanidis, P. J. Cox, A. Kaltzoglou, A. C. Tsipis, Eur. J. Inorg. Chem. 2006, 334-344;
  • 26
    • 33745205589 scopus 로고    scopus 로고
    • P. J. Cox, A. Kaltzoglou, P. Aslanidis, Inorg. Chim. Acta 2006, 359, 3183-3190. For these series, the P - Cu - P angles for dppbz (86.7°), dppp (99.6°) and Xantphos (113.2°) were taken from the X-ray structures.
    • c) P. J. Cox, A. Kaltzoglou, P. Aslanidis, Inorg. Chim. Acta 2006, 359, 3183-3190. For these series, the P - Cu - P angles for dppbz (86.7°), dppp (99.6°) and Xantphos (113.2°) were taken from the X-ray structures.
  • 30
    • 65349138827 scopus 로고    scopus 로고
    • Dppe gave complete conversion in the reaction of 2a as well.
    • Dppe gave complete conversion in the reaction of 2a as well.
  • 33
    • 65349173485 scopus 로고    scopus 로고
    • [11c]. This value can be compared with the angle of dppp (103.6°) and that of dppf (111.3 °).
    • [11c]. This value can be compared with the angle of dppp (103.6°) and that of dppf (111.3 °).
  • 34
    • 65349194917 scopus 로고    scopus 로고
    • The reaction did not proceed further even after a longer reaction time. Incomplete consumption of the starting material makes it difficult to cleanly separate the borylated product from the starting material. A ~72% yield was obtained by NMR analysis of a coelut-ed mixture of 2k and 3k.
    • The reaction did not proceed further even after a longer reaction time. Incomplete consumption of the starting material makes it difficult to cleanly separate the borylated product from the starting material. A ~72% yield was obtained by NMR analysis of a coelut-ed mixture of 2k and 3k.
  • 35
    • 65349135813 scopus 로고    scopus 로고
    • Only reactions with tertiary alkyl amides were reported. The boration reactions of β-phenyl-substituted amides were not reported either
    • Only reactions with tertiary alkyl amides were reported. The boration reactions of β-phenyl-substituted amides were not reported either.
  • 38
    • 0347131086 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2004, 43, 317-320;
    • (2004) Angew. Chem. Int. Ed , vol.43 , pp. 317-320
  • 41
    • 65349131758 scopus 로고    scopus 로고
    • An alternative activation procedure in which CuCl, NaO-t-Bu, ligand and diboron are mixed and stirred altogether for 15 min in THF is equally effective
    • An alternative activation procedure in which CuCl, NaO-t-Bu, ligand and diboron are mixed and stirred altogether for 15 min in THF is equally effective.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.