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Volumn 11, Issue 2, 2009, Pages 345-347

Copper-facilitated Suzuki reactions: Application to 2-heterocyclic boronates

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; COPPER; HETEROCYCLIC COMPOUND;

EID: 61449159817     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802556f     Document Type: Article
Times cited : (172)

References (28)
  • 1
    • 2042507954 scopus 로고    scopus 로고
    • Suzuki reviews: (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
    • Suzuki reviews: (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
  • 3
    • 34250690291 scopus 로고    scopus 로고
    • For Suzuki reactions with heterocyclic boronates, see: a
    • For Suzuki reactions with heterocyclic boronates, see: (a) Campeau, L.-C.; Fagnou, K. Chem. Soc. Rev. 2007, 36, 1058-1068.
    • (2007) Chem. Soc. Rev , vol.36 , pp. 1058-1068
    • Campeau, L.-C.1    Fagnou, K.2
  • 18
  • 19
    • 41449094998 scopus 로고    scopus 로고
    • For a recent example of DOE applied to a Pd-catalyzed reaction, see
    • For a recent example of DOE applied to a Pd-catalyzed reaction, see: Denmark, S. E.; Butler, C. R. J. Am. Chem. Soc. 2008, 130, 3690-3704.
    • (2008) J. Am. Chem. Soc , vol.130 , pp. 3690-3704
    • Denmark, S.E.1    Butler, C.R.2
  • 20
    • 62149114906 scopus 로고    scopus 로고
    • Though several substrates gave complete conversion within 1 h, reactions were continued to 16 h as a general protocol. Alternatively, reactions could be conducted using mircowave irradiation at 160 °C and were typically complete in 20 min
    • Though several substrates gave complete conversion within 1 h, reactions were continued to 16 h as a general protocol. Alternatively, reactions could be conducted using mircowave irradiation at 160 °C and were typically complete in 20 min.
  • 21
    • 34247882697 scopus 로고    scopus 로고
    • A similar phenomenon with C-H insertions was reported: Lewis, J. C.; Bergman, R. G.; Ellman, J. A J. Am. Chem. Soc. 2007, 129, 5332-5333.
    • A similar phenomenon with C-H insertions was reported: Lewis, J. C.; Bergman, R. G.; Ellman, J. A J. Am. Chem. Soc. 2007, 129, 5332-5333.
  • 22
    • 62149112635 scopus 로고    scopus 로고
    • This homocoupling is also associated with loss of Cu(I) from the catalytic cycle. Use of Cu2O minimizes homocoupling and enables a catalytic copper reaction, as 87% yield is achieved in entry 1, Table 1 with 10 mol, Cu2O. Conversions are substrate dependent, and efforts to develop more robust catalytic copper conditions are ongoing
    • 2O. Conversions are substrate dependent, and efforts to develop more robust catalytic copper conditions are ongoing.
  • 25
    • 62149098534 scopus 로고    scopus 로고
    • 2 and dppf due to competing homocoupling of the preformed 2-pyridylcopper species.
    • 2 and dppf due to competing homocoupling of the preformed 2-pyridylcopper species.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.