4.8 Article

Decarboxylative Allylation using Sulfones as Surrogates of Alkanes

Journal

ORGANIC LETTERS
Volume 10, Issue 20, Pages 4657-4660

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol801951e

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Funding

  1. National Institute of General Medical Sciences [1R01GM079644]

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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 a-sulfonyl anion is rate-limiting. Furthermore, the anion is formed reglospecifically under formally neutral conditions.

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