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Volumn 80, Issue 9, 2007, Pages 1814-1823

Cationic palladium complex-catalyzed hydrosilylative cross-coupling of alkynes with alkenes. 1,4-addition of triehlorosilane to form 4-silyl-1-butene framework

Author keywords

[No Author keywords available]

Indexed keywords

CARBOPALLADATION; CATALYTIC CYCLES; CATIONIC PALLADIUM COMPLEXES; COUPLING PATTERNS; CROSS COUPLINGS; PHOSPHINE LIGANDS; TWO TYPES;

EID: 44649187147     PISSN: 00092673     EISSN: 13480634     Source Type: Journal    
DOI: 10.1246/bcsj.80.1814     Document Type: Article
Times cited : (2)

References (58)
  • 11
    • 17744395347 scopus 로고    scopus 로고
    • For a review on addition of metalloid hydrides to alkynes, see
    • For a review on addition of metalloid hydrides to alkynes, see: B. M. Trost, Z. T. Ball, Synthesis 2005, 853.
    • (2005) Synthesis , pp. 853
    • Trost, B.M.1    Ball, Z.T.2
  • 26
    • 0010343399 scopus 로고    scopus 로고
    • 0-catalyzed dimerization of 1-alkynes, see: M. F. Lappert, T. A. Nile, S. Takahashi, J. Organomet. Chem. 1974, 72, 425.
    • 0-catalyzed dimerization of 1-alkynes, see: M. F. Lappert, T. A. Nile, S. Takahashi, J. Organomet. Chem. 1974, 72, 425.
  • 40
    • 58149316788 scopus 로고    scopus 로고
    • In the chemical formula, the designations α or β and 1 or 2 refer to the carbopalladation that occur at α or β position of the 1-alkyne employed, and C-Si bond occurring at terminal or internal carbon of the 1-alkene counterpart, respectively
    • In the chemical formula, the designations α or β and 1 or 2 refer to the carbopalladation that occur at α or β position of the 1-alkyne employed, and C-Si bond occurring at terminal or internal carbon of the 1-alkene counterpart, respectively.
  • 41
    • 58149277906 scopus 로고    scopus 로고
    • Immediate reaction products consist of α's (> 90%), a little β isomer (<5%) and others on the basis of GLC analysis, the latter two being hardly isolated at this stage.
    • Immediate reaction products consist of α's (> 90%), a little β isomer (<5%) and others on the basis of GLC analysis, the latter two being hardly isolated at this stage.
  • 42
    • 0036032368 scopus 로고    scopus 로고
    • 3 = tris{2,2″, 6,6″ - tetramethyl-m-terphenyl-5′-yl}-phosphine: a) K. Goto, Y. Ohzu, H. Sato, T. Kawashima, Phosphorus, Sulfur Silicon Relat. Elem. 2002, 177, 2179.
    • 3 = tris{2,2″, 6,6″ - tetramethyl-m-terphenyl-5′-yl}-phosphine: a) K. Goto, Y. Ohzu, H. Sato, T. Kawashima, Phosphorus, Sulfur Silicon Relat. Elem. 2002, 177, 2179.
  • 44
    • 58149277893 scopus 로고    scopus 로고
    • In this regard, it should be mentioned that, in the hydrosilylative cross-coupling of 1-heptyne with 1-hexene (3 equiv) in the presence of catalyst A, P(C6F5)3 caused very rapid conversion at room temperature, giving rise to products (55% yield) in 7a (α-l):9a (β-1, 22:78 (see, Table 3, Entry 3, footnote e, Thus, the fact that phenylacetylene, 1b (α-1, 2b (α-2, 3b (β-l, 85:15 (Table 1, Entry 5, and 1-heptyne show contrasting regioselectivities well reinforces that P(C6F5)3 as a ligand exhibits a reversed electronic effect on the hydropalladation step for these two alkynes
    • 3 as a ligand exhibits a reversed electronic effect on the hydropalladation step for these two alkynes.
  • 45
    • 58149306522 scopus 로고    scopus 로고
    • 3-Butyl-2-methylenebutanolide = 4-Butyl-3-methylene-4,5-dihydro-2(3H) furanone: E. Roeder, H. Krauss, Ann. Chim. 1992, 177.
    • a) 3-Butyl-2-methylenebutanolide = 4-Butyl-3-methylene-4,5-dihydro-2(3H) furanone: E. Roeder, H. Krauss, Ann. Chim. 1992, 177.
  • 46
    • 0001506010 scopus 로고    scopus 로고
    • 2-Methylene-3-phenylbutanolide: H. Nishiyama, H. Yokoyama, S. Narimatsu, K. Itoh, Tetrahedron Lett. 1982, 23, 1267.
    • b) 2-Methylene-3-phenylbutanolide: H. Nishiyama, H. Yokoyama, S. Narimatsu, K. Itoh, Tetrahedron Lett. 1982, 23, 1267.
  • 47
    • 0035831161 scopus 로고    scopus 로고
    • Reversivility of the hydropalladation in the Pd-catalyzed alkadiynes has not been established. However, reversible silylpalladation in the case of alkadienes under similar reaction conditions are discussed. See
    • Reversivility of the hydropalladation in the Pd-catalyzed alkadiynes has not been established. However, reversible silylpalladation in the case of alkadienes under similar reaction conditions are discussed. See: X. Wang, H. Chakrapani, C. N. Stengone, R. A. Widenhoefer, J. Org. Chem. 2001, 66, 1755.
    • (2001) J. Org. Chem , vol.66 , pp. 1755
    • Wang, X.1    Chakrapani, H.2    Stengone, C.N.3    Widenhoefer, R.A.4
  • 48
    • 58149296714 scopus 로고    scopus 로고
    • With regard to this discussion, Hayashi et al. have observed that the reaction of [Pd(η3-C3H5)Cl]2 with HSiEt3 in the presence of a diphosphine generates a Pd 0L2 species together with ClSiEt3 and propene. The reaction with HSiCl3 and PPh3 should also produce a Pd0 species. See: Y. Uozumi, H. Tsuji, T. Hayashi, J. Org. Chem. 1998, 63, 6137; Hydrosilylation of 1,5- and 1,3-cyclooctadiene has long been known to be catalyzed easily by various types of Pt catalysts: K. Yamamoto, M. Kumada, J. Organometal. Chem. 1968, 13, 131
    • 0 species. See: Y. Uozumi, H. Tsuji, T. Hayashi, J. Org. Chem. 1998, 63, 6137; Hydrosilylation of 1,5- and 1,3-cyclooctadiene has long been known to be catalyzed easily by various types of Pt catalysts: K. Yamamoto, M. Kumada, J. Organometal. Chem. 1968, 13, 131.
  • 49
    • 58149277902 scopus 로고    scopus 로고
    • 3 will be discussed elsewhere: N. Takaoka, B.S. Thesis, Tokyo University of Science, Yamaguchi, 2004.
    • 3 will be discussed elsewhere: N. Takaoka, B.S. Thesis, Tokyo University of Science, Yamaguchi, 2004.
  • 51
    • 85022586647 scopus 로고    scopus 로고
    • A cationic arylpalladium species is known to undergo a facile alkene insertion in the Mizoroki-Heck reaction: F. Ozawa, T. Hayashi, J. Am. Chem. Soc. 1991, 113, 1417;
    • A cationic arylpalladium species is known to undergo a facile alkene insertion in the Mizoroki-Heck reaction: F. Ozawa, T. Hayashi, J. Am. Chem. Soc. 1991, 113, 1417;
  • 52
    • 58149277905 scopus 로고    scopus 로고
    • For a relevant review, see
    • For a relevant review, see: T. Nishikata, N. Miyaura, Shokubai 2005, 47, 619.
    • (2005) Shokubai , vol.47 , pp. 619
    • Nishikata, T.1    Miyaura, N.2
  • 55
    • 58149311652 scopus 로고    scopus 로고
    • 3 (X = Cl or OEt) and not consonant with those by CAS (9CI).
    • 3 (X = Cl or OEt) and not consonant with those by CAS (9CI).
  • 56
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    • and references cited therein
    • B. M. Trost, Z. T. Ball, J. Am. Chem. Soc. 2001, 123, 12726, and references cited therein.
    • (2001) J. Am. Chem. Soc , vol.123 , pp. 12726
    • Trost, B.M.1    Ball, Z.T.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.