4.4 Article

Tin-free radical carbon-carbon bond-forming reactions based on α-scission of alkylsulfonyl radicals

Journal

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
Volume 80, Issue 5, Pages 809-822

Publisher

CHEMICAL SOC JAPAN
DOI: 10.1246/bcsj.80.809

Keywords

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Funding

  1. National Research Foundation of Korea [과06A1506, R11-1999-056-01008-0] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)

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Tin-free radical reactions based on a-scission of alkylsulfonyl radicals are very useful for the formation of carbon-carbon bonds and include allylation, acylation, cyanation, vinylation, and carbonylation. For secondary, tertiary, and benzylic radicals, it is possible to use the corresponding iodides as precursors but the primary radicals still require the use of phenyl tellurides or alkyl allyl sulfones. Especially, alkyl allyl sulfones are highly efficient and most reliable primary alkyl radical precursors for the further formation of carbon-carbon bonds. The present approach is very useful for introducing various functional groups such as carbonyl and alkenyl groups under tin-free conditions.

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