메뉴 건너뛰기




Volumn 137, Issue 46, 2015, Pages 14812-14818

Mechanistic Studies Lead to Dramatically Improved Reaction Conditions for the Cu-Catalyzed Asymmetric Hydroamination of Olefins

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYST REGENERATION; CATALYSTS; COPPER; ELECTROSPRAY IONIZATION; HYDROCARBONS; MASS SPECTROMETRY; PHOSPHORUS COMPOUNDS; SPECTROSCOPIC ANALYSIS; STYRENE;

EID: 84948687858     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b10219     Document Type: Article
Times cited : (107)

References (80)
  • 1
    • 33745869897 scopus 로고    scopus 로고
    • Cambridge University Press: Cambridge.
    • Lawrence, S. A. Amines; Cambridge University Press: Cambridge, 2006.
    • (2006) Amines
    • Lawrence, S.A.1
  • 5
    • 84927127197 scopus 로고    scopus 로고
    • For a general review on late transition metal-catalyzed hydroaminations, see
    • For a general review on late transition metal-catalyzed hydroaminations, see: Huang, L.; Arndt, M.; Gooßen, K.; Heydt, H.; Gooßen, L. J. Chem. Rev. 2015, 115, 2596 10.1021/cr300389u
    • (2015) Chem. Rev. , vol.115 , pp. 2596
    • Huang, L.1    Arndt, M.2    Gooßen, K.3    Heydt, H.4    Gooßen, L.J.5
  • 34
    • 75749092923 scopus 로고    scopus 로고
    • Other CuH-catalyzed processes have observed fractional order dependencies on the catalyst, see
    • Other CuH-catalyzed processes have observed fractional order dependencies on the catalyst, see: Issenhuth, J.-T.; Notter, F.-P.; Dagorne, S.; Dedieu, A.; Bellemin-Laponnaz, S. Eur. J. Inorg. Chem. 2010, 2010, 529 10.1002/ejic.200900961
    • (2010) Eur. J. Inorg. Chem. , vol.2010 , pp. 529
    • Issenhuth, J.-T.1    Notter, F.-P.2    Dagorne, S.3    Dedieu, A.4    Bellemin-Laponnaz, S.5
  • 38
    • 80051745492 scopus 로고    scopus 로고
    • For a review of KIEs in organometallic reactions that includes KIE studies with silanes, see
    • For a review of KIEs in organometallic reactions that includes KIE studies with silanes, see: Gómez-Gallego, M.; Sierra, M. A. Chem. Rev. 2011, 111, 4857 10.1021/cr100436k
    • (2011) Chem. Rev. , vol.111 , pp. 4857
    • Gómez-Gallego, M.1    Sierra, M.A.2
  • 44
    • 79251477873 scopus 로고    scopus 로고
    • Bertrand has also synthesized a room temperature stable cyclic (alkyl)-(amino)carbene (CAAC) copper(I) hydride dimer
    • Bertrand has also synthesized a room temperature stable cyclic (alkyl)-(amino)carbene (CAAC) copper(I) hydride dimer: Frey, G. D.; Donnadieu, B.; Soleilhavoup, M.; Bertrand, G. Chem.-Asian J. 2011, 6, 402 10.1002/asia.201000576
    • (2011) Chem. - Asian J. , vol.6 , pp. 402
    • Frey, G.D.1    Donnadieu, B.2    Soleilhavoup, M.3    Bertrand, G.4
  • 45
    • 26844454922 scopus 로고    scopus 로고
    • Lipshutz has reported spectroscopic evidence for a (DTBM-SEGPHOS)CuH complex
    • Lipshutz has reported spectroscopic evidence for a (DTBM-SEGPHOS)CuH complex: Lipshutz, B. H.; Frieman, B. A. Angew. Chem., Int. Ed. 2005, 44, 6345 10.1002/anie.200500800
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 6345
    • Lipshutz, B.H.1    Frieman, B.A.2
  • 52
    • 84948652648 scopus 로고    scopus 로고
    • Reference 9b.
    • Reference 9b.
  • 55
    • 84948649382 scopus 로고    scopus 로고
    • Reference 11.
    • Reference 11.
  • 56
    • 84948656011 scopus 로고    scopus 로고
    • Reference 13a.
    • Reference 13a.
  • 67
    • 84948697650 scopus 로고    scopus 로고
    • For a discussion of KIE studies in relation to β-hydride elimination, see reference 15.
    • For a discussion of KIE studies in relation to β-hydride elimination, see reference 15.
  • 71
    • 84899531906 scopus 로고    scopus 로고
    • A recent report noted that the activation barrier for CuH regeneration in the hydrosilylation of ketones correlated with the hydride character of the silane employed, which followed a trend similar to what we found with testing various silanes in the CuH-catalyzed hydroamination of styrene, see
    • A recent report noted that the activation barrier for CuH regeneration in the hydrosilylation of ketones correlated with the hydride character of the silane employed, which followed a trend similar to what we found with testing various silanes in the CuH-catalyzed hydroamination of styrene, see: Vergote, T.; Nahra, F.; Merschaert, A.; Riant, O.; Peeters, D.; Leyssens, T. Organometallics 2014, 33, 1953 10.1021/om401097q
    • (2014) Organometallics , vol.33 , pp. 1953
    • Vergote, T.1    Nahra, F.2    Merschaert, A.3    Riant, O.4    Peeters, D.5    Leyssens, T.6
  • 72
    • 84948688710 scopus 로고    scopus 로고
    • Referencce 23b.
    • Referencce 23b.
  • 73
    • 84948671097 scopus 로고    scopus 로고
    • Referencce 7a.
    • Referencce 7a.
  • 80
    • 34247525138 scopus 로고    scopus 로고
    • Multiple mechanistic pathways are possible for C-N bond formation. For a mechanistic study on a related Cu-catalyzed amination process, see
    • Multiple mechanistic pathways are possible for C-N bond formation. For a mechanistic study on a related Cu-catalyzed amination process, see: Campbell, M. J.; Johnson, J. S. Org. Lett. 2007, 9, 1521 10.1021/ol0702829
    • (2007) Org. Lett. , vol.9 , pp. 1521
    • Campbell, M.J.1    Johnson, J.S.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.