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Volumn 74, Issue 3, 2009, Pages 1415-1417

Zinc-catalyzed nucleophilic substitution reaction of chlorosilanes with organomagnesium reagents

Author keywords

[No Author keywords available]

Indexed keywords

CHLOROSILANES; FUNCTIONALIZED; MILD REACTION CONDITIONS; NUCLEOPHILIC SUBSTITUTION REACTIONS; ORGANOMAGNESIUM;

EID: 64549110941     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo802433t     Document Type: Article
Times cited : (47)

References (25)
  • 1
    • 34548403847 scopus 로고    scopus 로고
    • Houben-Weyl, Fleming, I, Ed, Georg Thieme Verlag: Stuttgart, Germany, Chapter. 4.4
    • (a) Science of Synthesis (Houben-Weyl); Fleming, I., Ed.; Georg Thieme Verlag: Stuttgart, Germany, 2002; Vol. 4, Chapter. 4.4.
    • (2002) Science of Synthesis , vol.4
  • 6
    • 64549134580 scopus 로고    scopus 로고
    • Historically, alkylations of halosilane were demonstrated for the first time by using diorganozinc reagents under harsh reaction conditions
    • Historically, alkylations of halosilane were demonstrated for the first time by using diorganozinc reagents under harsh reaction conditions:
  • 9
    • 64549135021 scopus 로고    scopus 로고
    • Treatment of 1a with zinc fluoride in THF provided Me2PhSiF, which is more reactive toward the nucleophilic substitution with 2a. Thus, the mechanism of activating chlorosilane 1a may be different from that of other zinc salts
    • Treatment of 1a with zinc fluoride in THF provided Me2PhSiF, which is more reactive toward the nucleophilic substitution with 2a. Thus, the mechanism of activating chlorosilane 1a may be different from that of other zinc salts.
  • 10
    • 64549117309 scopus 로고    scopus 로고
    • The reaction of chlorotriethylsilane proceeded smoothly in the presence of a catalytic amount of silver nitrate, see ref 3
    • The reaction of chlorotriethylsilane proceeded smoothly in the presence of a catalytic amount of silver nitrate, see ref 3.
  • 12
    • 64549159291 scopus 로고    scopus 로고
    • THF was the best solvent in the reactions with vinyl-, benzyl-, and allylmagnesium reagents. 1,4-Dioxane retarded the reactions.
    • THF was the best solvent in the reactions with vinyl-, benzyl-, and allylmagnesium reagents. 1,4-Dioxane retarded the reactions.
  • 13
    • 64549120099 scopus 로고    scopus 로고
    • Treatment of chloromethyldiphenylsilane with 4-pentenylmagnesium bromide for 3 h provided the desired product in 32% yield in the absence of any zinc salts. However, no acceleration of the reaction was observed even when zinc salts were added.
    • Treatment of chloromethyldiphenylsilane with 4-pentenylmagnesium bromide for 3 h provided the desired product in 32% yield in the absence of any zinc salts. However, no acceleration of the reaction was observed even when zinc salts were added.
  • 14
    • 0000444566 scopus 로고    scopus 로고
    • Ultrasound irradiation was required for the synthesis of allylsilane 4f, see: Hagen, G.; Mayr, H. J. Am. Chem. Soc. 1991, 113, 4954-4961.
    • Ultrasound irradiation was required for the synthesis of allylsilane 4f, see: Hagen, G.; Mayr, H. J. Am. Chem. Soc. 1991, 113, 4954-4961.
  • 15
    • 4544311534 scopus 로고    scopus 로고
    • Krasovskiy, A.; Knochel, P. Ansew. Chem., Int. Ed. 2004, 43, 3333 3336.
    • Krasovskiy, A.; Knochel, P. Ansew. Chem., Int. Ed. 2004, 43, 3333 3336.
  • 16
    • 33746929105 scopus 로고    scopus 로고
    • For recent examples of zincate chemistry see: a
    • For recent examples of zincate chemistry see: (a) Hatano, M.; Suzuki, S.; Ishihara, K. J. Am. Chem. Soc. 2006, 128, 9998-9999.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 9998-9999
    • Hatano, M.1    Suzuki, S.2    Ishihara, K.3
  • 17
    • 53549097937 scopus 로고    scopus 로고
    • Studte, C.; Breit, B. Ansew. Chem., Int. Ed. 2008, 47, 5451-5455.
    • (b) Studte, C.; Breit, B. Ansew. Chem., Int. Ed. 2008, 47, 5451-5455.
  • 18
    • 34250771010 scopus 로고    scopus 로고
    • Mulvey, R. E.; Mongin, F.; Uchiyama, M.; Kondo, K. Ansew. Chem., Int. Ed. 2007, 47, 3802-3824.
    • (c) Mulvey, R. E.; Mongin, F.; Uchiyama, M.; Kondo, K. Ansew. Chem., Int. Ed. 2007, 47, 3802-3824.
  • 25
    • 64549149257 scopus 로고    scopus 로고
    • Commercially available
    • Commercially available.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.