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Volumn 43, Issue 38, 2004, Pages 5052-5055

Distannylation of strained carbon-carbon triple bonds catalyzed by a palladium complex

Author keywords

Arynes; Cycloalkynes; Homogeneous catalysis; Palladium; Tin

Indexed keywords

CATALYSIS; CATALYSTS; PALLADIUM; SUBSTRATES;

EID: 4944244569     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200460189     Document Type: Article
Times cited : (97)

References (44)
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    • b) S. L. Buchwald, R. D. Broene, in Comprehensive Organometallic Chemistry II, Vol. 12 (Eds.: E. W. Able, F. G. A. Stone, G. Wilkinson), Pergamon, Oxford, 1995, pp. 771-784;
    • (1995) Comprehensive Organometallic Chemistry II , vol.12 , pp. 771-784
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  • 4
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    • c) M. A. Bennett, H. P. Schwemlein, Angew. Chem. 1989, 101, 1349; Angew. Chem. Int. Ed. Engl. 1989, 28, 1296;
    • (1989) Angew. Chem. Int. Ed. Engl. , vol.28 , pp. 1296
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    • a) D. Peña S. Escudero, D. Pérez, E. Guitián, L. Castedo, Angew. Chem. 1998, 110, 2804; Angew. Chem. Int. Ed. 1998, 37, 2659;
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 2659
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    • c) E. Yoshikawa, Y. Yamamoto, Angew. Chem. 2000, 112, 185; Angew. Chem. Int. Ed. 2000, 39, 173;
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 173
  • 19
    • 0001034345 scopus 로고    scopus 로고
    • Reviews on the addition of σ bonds to unsaturated organic compounds: a) I. Beletskaya, C. Moberg, Chem. Rev. 1999, 99, 3435;
    • (1999) Chem. Rev. , vol.99 , pp. 3435
    • Beletskaya, I.1    Moberg, C.2
  • 25
    • 4944266668 scopus 로고    scopus 로고
    • note
    • A palladium-isocyanide complex has been shown by Ito and co-workers to be an efficient catalyst for disilylation, silylstannylation, or silylboration of unsaturated organic compounds such as alkynes and alkenes, see Ref. [6b].
  • 29
    • 4944260368 scopus 로고    scopus 로고
    • note
    • The combination of CsF and MeCN has been employed frequently in the catalytic transformations of arynes, see Ref. [3-5] and [7a].
  • 30
    • 4944251276 scopus 로고    scopus 로고
    • note
    • No trace of the distannylation products of these arynes was found in the reaction with 1a.
  • 34
    • 4944236432 scopus 로고    scopus 로고
    • note
    • Oxidative addition of a distannane to a palladium(0) complex has been proposed to be an initiation step in the distannylation of alkynes, see Ref. [6a].
  • 37
    • 4944222281 scopus 로고    scopus 로고
    • note
    • The configuration of 4a (cis or trans) could not be elucidated.
  • 40
    • 0142258788 scopus 로고    scopus 로고
    • The palladium-catalyzed carbostannylation of arynes has also been reported to proceed via palladacycle 6: T. Matsubara, Organometallics 2003, 22, 4297; see also Ref. [7a].
    • (2003) Organometallics , vol.22 , pp. 4297
    • Matsubara, T.1
  • 41
    • 4944247378 scopus 로고    scopus 로고
    • note
    • 2] with 2a and KF/[18]crown-6 was unsuccessful.
  • 42
    • 4944240171 scopus 로고    scopus 로고
    • note
    • The five-membered palladacycle 7 has been proposed to be a key intermediate in the palladium-catalyzed trimerization of arynes, see Ref. [2a].
  • 43
    • 0033526336 scopus 로고    scopus 로고
    • 0 complex and 2 mol of an alkyne, with an organostannane has been demonstrated to be a key step in the palladium-catalyzed dimerization- carbostannylation of alkynes: a) E. Shirakawa, H. Yoshida, Y. Nakao, T. Hiyama, J. Am. Chem. Soc. 1999, 121, 4290;
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 4290
    • Shirakawa, E.1    Yoshida, H.2    Nakao, Y.3    Hiyama, T.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.