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Volumn 10, Issue 1, 2008, Pages 129-131

Oxidative coupling of arylboronic acids with arenes via Rh-catalyzed direct C-H arylation

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; RHODIUM;

EID: 38349133722     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702659a     Document Type: Article
Times cited : (156)

References (40)
  • 1
    • 0000718373 scopus 로고    scopus 로고
    • (a) Pu, L. Chem. Rev. 1998, 98, 2405.
    • (1998) Chem. Rev , vol.98 , pp. 2405
    • Pu, L.1
  • 9
    • 34249936878 scopus 로고    scopus 로고
    • C-H activation of both coupling partners: Stuart, D. R.; Fagnou, K. Science 2007, 316, 1172.
    • C-H activation of both coupling partners: Stuart, D. R.; Fagnou, K. Science 2007, 316, 1172.
  • 22
    • 33749509027 scopus 로고    scopus 로고
    • Alkyl - aryl coupling: (a) Chen, X.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 12634.
    • Alkyl - aryl coupling: (a) Chen, X.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 12634.
  • 24
    • 19744365933 scopus 로고    scopus 로고
    • Oxidative C - H activation using Pd: (a) ref 6. (b) Kalyani, D.; Deprez, N. R.; Desai, L. V.; Sanford, M. S. J. Am. Chem. Soc. 2005, 127, 7330.
    • Oxidative C - H activation using Pd: (a) ref 6. (b) Kalyani, D.; Deprez, N. R.; Desai, L. V.; Sanford, M. S. J. Am. Chem. Soc. 2005, 127, 7330.
  • 27
    • 0027411812 scopus 로고    scopus 로고
    • Oxidative coupling of phenols using Rh: Barrett, A. G. M.; Itoh, T.; Wallace, E. M. Tetrahedron Lett. 1993, 34, 2233.
    • Oxidative coupling of phenols using Rh: Barrett, A. G. M.; Itoh, T.; Wallace, E. M. Tetrahedron Lett. 1993, 34, 2233.
  • 39
    • 38349114363 scopus 로고    scopus 로고
    • 4Sn and tetraphenylborates have been reported; see refs 12c and 11a. However, in these reactions, no oxidant was used. As suggested, insertion of a Rh(I) complex into a C - H aryl bond (aryl-H activation) leads to a HRh(III)aryl species which undergoes further reaction. Our process is different since an external oxidant is necessary and the C-H-activation probably occurs via electrophilic aromatic substitution. In fact, without oxidant our reactions did not proceed.
    • 4Sn and tetraphenylborates have been reported; see refs 12c and 11a. However, in these reactions, no oxidant was used. As suggested, insertion of a Rh(I) complex into a C - H aryl bond (aryl-H activation) leads to a HRh(III)aryl species which undergoes further reaction. Our process is different since an external oxidant is necessary and the "C-H-activation" probably occurs via electrophilic aromatic substitution. In fact, without oxidant our reactions did not proceed.
  • 40
    • 34147156671 scopus 로고    scopus 로고
    • Rh(I) carboxylates can be oxidized with Cu(OAc)2 to the corresponding Rh(III) complexes, which subsequently undergo directed C - H arylation: Ueura, K.; Satoh, T.; Miura, M. Org. Lett. 2007, 9, 1407.
    • Rh(I) carboxylates can be oxidized with Cu(OAc)2 to the corresponding Rh(III) complexes, which subsequently undergo directed C - H arylation: Ueura, K.; Satoh, T.; Miura, M. Org. Lett. 2007, 9, 1407.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.