메뉴 건너뛰기




Volumn 44, Issue 29, 2005, Pages 4608-4611

Synthesis of seven-membered-ring ketones by arylative ring expansion of alkyne-substituted cyclobutanones

Author keywords

Boron; Elimination; Ketones; Rhodium; Ring expansion

Indexed keywords

CATALYSIS; CHEMICAL BONDS; RHODIUM COMPOUNDS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

EID: 22744439488     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200500799     Document Type: Article
Times cited : (89)

References (31)
  • 4
    • 0034246704 scopus 로고    scopus 로고
    • d) L. Yet, Chem. Rev. 2000, 100, 2963-3007.
    • (2000) Chem. Rev. , vol.100 , pp. 2963-3007
    • Yet, L.1
  • 14
    • 0032542313 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 1998, 37, 3279-3281;
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 3279-3281
  • 17
    • 22744449383 scopus 로고    scopus 로고
    • note
    • 4 gave 2-(2-bromophenyl)cyclobutanone (58%). Introduction of a but-1-ynyl moiety by palladium-catalyzed coupling furnished 1a (55%). See Supporting Information for details.
  • 18
    • 0035914022 scopus 로고    scopus 로고
    • Triphenylboroxin and water were used to generate phenylboronic acid in situ, see: a) T. Senda, M. Ogasawara, T. Hayashi, J. Org. Chem. 2001, 66, 6852-6856;
    • (2001) J. Org. Chem. , vol.66 , pp. 6852-6856
    • Senda, T.1    Ogasawara, M.2    Hayashi, T.3
  • 24
    • 1342302388 scopus 로고    scopus 로고
    • For a review on β-carbon eliminations from palladium(n) cyclobutanolates, see: T. Nishimura, S. Uemura, Synlett 2004, 201-216.
    • (2004) Synlett , pp. 201-216
    • Nishimura, T.1    Uemura, S.2
  • 25
    • 0037467052 scopus 로고    scopus 로고
    • For examples of related migrations of transition metals leading to enolates, see: a) H. Qian, R. A. Widenhoefer, J. Am. Chem. Soc. 2003, 125, 2056-2057;
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 2056-2057
    • Qian, H.1    Widenhoefer, R.A.2
  • 30
    • 22744437429 scopus 로고    scopus 로고
    • note
    • The reaction with o-tolylboroxin resulted in the formation of a complex mixture of products, in which 1,2-adduct 4 was the only identifiable product.
  • 31
    • 22744442130 scopus 로고    scopus 로고
    • note
    • Ring expansion by β-carbon elimination failed to occur even when the isolated 5 ja was heated at 160°C in the presence of the rhodium catalyst.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.