Indium(III) salt promoted intramolecular addition of allylsilanes to unactivated alkynes

Synlett

Volumn , Issue 12, 2006, Pages 1883-1886

  Miura, Katsukiyo ^a   Fujisawa, Naoki ^a   Toyohara, Sayaka ^a   Hosomi, Akira ^b  

^a UNIVERSITY OF TSUKUBA   (Japan)

^b National Institution for Academic Degrees and University Evaluation Tokyo   (Japan)

Author keywords

Alkynes; Catalysis; Cyclizations; Indium; Silicon

Indexed keywords

ALKYNE DERIVATIVE; ALLYLSILANE DERIVATIVE; INDIUM; INDIUM 3 SALT; LEWIS ACID; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; STOICHIOMETRY;

EID: 33747040276     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-947348     Document Type: Article

References (22)

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12. (b) The original method, in which CuCN was not used, resulted in low reproducibility. Use of the copper catalyst achieved high yield of the desired adduct with good reproducibility.
13. The competitive desilylation is attributable to higher nucleophilicity of the methallylsilane moiety. See: Hagen, G.; Mayr, H. J. Am. Chem. Soc. 1991, 113, 4954.
14. 3.
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21. 3SiCl and adventitious water may cause the in situ protonation of vinylindium 4.
22. 2O resulted in low D-content (<5%) of 2a.