Aliphatic Radical Relay Heck Reaction at Unactivated C(sp³ )-H Sites of Alcohols.

ABSTRACT: The Mizoroki-Heck reaction is one of the most efficient methods for alkenylation of aryl, vinyl, and alkyl halides. Given its innate nature, this protocol requires the employment of compounds possessing a halogen atom at the site of functionalization. However, the accessibility of organic molecules possessing a halogen atom at a particular site in aliphatic systems is extremely limited. Thus, a protocol that allows a Heck reaction to occur at a specific nonfunctionalized C(sp³ )-H site is desirable. Reported here is a radical relay Heck reaction which allows selective remote alkenylation of aliphatic alcohols at unactivated β-, γ-, and δ-C(sp³ )-H sites. The use of an easily installed/removed Si-based auxiliary enables selective I-atom/radical translocation events at

SUBMITTER: Chuentragool P 

PROVIDER: S-EPMC6359925 | biostudies-literature | 2019 Feb

REPOSITORIES: biostudies-literature