In:
European Journal of Organic Chemistry, Wiley, Vol. 2005, No. 10 ( 2005-05), p. 1965-1968
Abstract:
Trialkylsilyl groups play an important role as effective protecting groups in organic synthesis. Various O, N, and C nucleophilic sites can be protected by trialkylsilyl groups to control the selectivity of reactions. The nucleophilic attack of a fluoride anion on a silyl group is recognized as one of the most useful methods for desilylation. The activation of the nucleophile–silicon bond is important not only for desilylation but also for the generation of a reactive nucleophilic anion to achieve a new bond formation. The phosphazene bases developed by Schwesinger are known to be strong non‐metallic organic bases. Among them, the t Bu‐P4 base has been used for various selective deprotonative transformations, although the ability of t Bu‐P4 base to activate silylated nucleophiles has not yet been shown. A novel catalytic activation of various O, N, and C nucleophile–silicon bonds using t Bu‐P4 base was investigated to perform nucleophilic reactions with various electrophiles. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
Type of Medium:
Online Resource
ISSN:
1434-193X
,
1099-0690
DOI:
10.1002/ejoc.v2005:10
DOI:
10.1002/ejoc.200500087
Language:
English
Publisher:
Wiley
Publication Date:
2005
detail.hit.zdb_id:
1475010-7
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