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Decarboxylative allylation using sulfones as surrogates of alkanes.

ABSTRACT: Alpha-sulfonyl functional groups are traceless activating groups that facilitate catalytic decarboxylative allylations in high yield yet can be cleaved to allow the synthesis of simple allylated alkanes. Substrate studies suggest that decarboxylation to form an alpha-sulfonyl anion is rate-limiting. Furthermore, the anion is formed regiospecifically under formally neutral conditions.

SUBMITTER: Weaver JD

PROVIDER: S-EPMC2754783 | biostudies-literature | 2008 Oct

REPOSITORIES: biostudies-literature

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Decarboxylative allylation using sulfones as surrogates of alkanes.

Weaver Jimmie D JD Tunge Jon A JA

Organic letters 20080912 20

Alpha-sulfonyl functional groups are traceless activating groups that facilitate catalytic decarboxylative allylations in high yield yet can be cleaved to allow the synthesis of simple allylated alkanes. Substrate studies suggest that decarboxylation to form an alpha-sulfonyl anion is rate-limiting. Furthermore, the anion is formed regiospecifically under formally neutral conditions. ...[more]

PMID: 18785744

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