메뉴 건너뛰기




Volumn 45, Issue 14, 2006, Pages 2271-2274

Regio- and stereoselective decarbonylative carbostannylation of alkynes catalyzed by Pd/C

Author keywords

C C coupling; Metalation; Palladium; Tin

Indexed keywords

CATALYSIS; CATALYST ACTIVITY; CHEMICAL REACTIONS; PALLADIUM;

EID: 33746281108     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200504283     Document Type: Article
Times cited : (29)

References (41)
  • 2
    • 0001522634 scopus 로고
    • (Eds.: B. M. Trost, I. Fleming, M. F. Semmelhack), Pergamon, New York
    • b) P. Knochel in Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Fleming, M. F. Semmelhack), Pergamon, New York, 1991, pp. 865-911;
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 865-911
    • Knochel, P.1
  • 13
    • 4544257657 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2004, 43, 3448-3451;
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 3448-3451
  • 16
    • 0001996468 scopus 로고    scopus 로고
    • The allylstannylation of alkynes through the nucleophilic addition of allylstannanes across alkynes activated by a Lewis acid is known, see: a) N. Asao, Y. Matsukawa, Y. Yamamoto, Chem. Commun. 1996, 1513-1514;
    • (1996) Chem. Commun. , pp. 1513-1514
    • Asao, N.1    Matsukawa, Y.2    Yamamoto, Y.3
  • 22
    • 0038336919 scopus 로고    scopus 로고
    • d) T. Matsubara, K. Hirao, Organometallics 2002, 21, 4482-4489; for allyl and acylstannanes, see references [2g] and [2e], respectively.
    • (2002) Organometallics , vol.21 , pp. 4482-4489
    • Matsubara, T.1    Hirao, K.2
  • 27
    • 0034029281 scopus 로고    scopus 로고
    • The palladium-catalyzed arylstannylation of norbornene using aryl(trichloro)stannanes has been proposed to proceed through the oxidative addition of an Ar-Sn bond to palladium(0) complexes, see: a) K. Fugami, Y. Mishiba, S. Hagiwara, D. Koyama, M. Kameyama, M. Kosugi, Synlett 2000, 553-555;
    • (2000) Synlett , pp. 553-555
    • Fugami, K.1    Mishiba, Y.2    Hagiwara, S.3    Koyama, D.4    Kameyama, M.5    Kosugi, M.6
  • 28
    • 0034986271 scopus 로고    scopus 로고
    • aryl- and alkenylstannanes undergo the palladium-catalyzed dimerization/carbostannylation of alkynes not through oxidative addition but through the reaction with palladacyclopentadienes; see: b) H. Yoshida, E. Shirakawa, Y. Nakao, Y. Honda, T. Hiyama, Bull. Chem. Soc. Jpn. 2001, 74, 637-647.
    • (2001) Bull. Chem. Soc. Jpn. , vol.74 , pp. 637-647
    • Yoshida, H.1    Shirakawa, E.2    Nakao, Y.3    Honda, Y.4    Hiyama, T.5
  • 29
    • 0000685605 scopus 로고
    • Acyl(tributyl)stannanes are readily prepared by the reaction of aldehydes with tributylstannylmagnesium or -lithium reagents, see: a) M. Kosugi, H. Naka, T. Sano, T. Migita, Bull. Chem. Soc. Jpn. 1987, 60, 3462-3464;
    • (1987) Bull. Chem. Soc. Jpn. , vol.60 , pp. 3462-3464
    • Kosugi, M.1    Naka, H.2    Sano, T.3    Migita, T.4
  • 31
    • 3643112634 scopus 로고
    • For decarbonylative 1,4-carbosilylation of 1,3-dienes through three-component coupling, see: a) Y. Obora, Y. Tsuji, T. Kawamura, J. Am. Chem. Soc. 1995, 117, 9814-9821;
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 9814-9821
    • Obora, Y.1    Tsuji, Y.2    Kawamura, T.3
  • 33
    • 33746322949 scopus 로고    scopus 로고
    • note
    • The use of other ethereal solvents, such as THF, 1,4-dioxane, 1,2-dimethoxyethane (DME), toluene, and dimethyl formamide (DMF), gave inferior results.
  • 35
    • 0000665822 scopus 로고
    • A similar regioselective insertion of propargyl pivalate into a H-Pt bond has been proposed, see: G. Stork, M. E. Jung, E. Colvin, Y. Noel, J. Am. Chem. Soc. 1974, 96, 3684-3686.
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 3684-3686
    • Stork, G.1    Jung, M.E.2    Colvin, E.3    Noel, Y.4
  • 36
    • 0001445927 scopus 로고
    • Acyl-palladium intermediates are reluctant to undergo decarbonylation (≈200°C), as observed in the palladium-catalyzed decarbonylation of acyl halides or aldehydes, whereas the presence of an alkene and/or a base accelerates decarbonylation in the decarbonylative coupling reaction of acid chlorides with alkenes; see reference [8] and a) J. O. Hawthorne, M. H. Wilt, J. Org. Chem. 1960, 25, 2215-2216;
    • (1960) J. Org. Chem. , vol.25 , pp. 2215-2216
    • Hawthorne, J.O.1    Wilt, M.H.2
  • 40
    • 33847085177 scopus 로고
    • No side products, such as a hydrostannylation product derived from β-hydride elimination, were observed during the reaction of tributyl(propanoyl)stannane (Table 2, entry 7), thus implying rapid reductive elimination from 6; for CO-induced reductive elimination, see: T. Yamamoto, J. Ishizu, T. Kohara, S. Komiya, A. Yamamoto, J. Am. Chem. Soc. 1980, 102, 3758-3764.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 3758-3764
    • Yamamoto, T.1    Ishizu, J.2    Kohara, T.3    Komiya, S.4    Yamamoto, A.5
  • 41
    • 33746290351 scopus 로고    scopus 로고
    • note
    • The reaction under identical conditions to entry 4 in Table 2 but under a CO atmosphere (1 atm) gave adduct 3i in less than 20% yield, and no trace amounts of a non-decarbonylative adduct, such as 8, was observed.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.