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Visible light-promoted ring-opening functionalization of unstrained cycloalkanols via inert C-C bond scission.

ABSTRACT: Described herein is a novel, useful, visible light-promoted ring-opening functionalization of unstrained cycloalkanols. Upon scission of an inert cyclic C-C ?-bond, a set of medium- and large-sized rings are readily brominated under mild reaction conditions to afford the corresponding distal bromo-substituted alkyl ketones that are hard to synthesize otherwise. The products are versatile building blocks, which are easily converted to other valuable molecules in one-step operation. This protocol is also applicable to the unprecedented ring-opening cyanation and alkynylation of unstrained cycloalkanols.

SUBMITTER: Wang D

PROVIDER: S-EPMC6050598 | biostudies-literature | 2018 Jul

REPOSITORIES: biostudies-literature

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Visible light-promoted ring-opening functionalization of unstrained cycloalkanols <i>via</i> inert C-C bond scission.

Wang Dongping D Mao Jincheng J Zhu Chen C

Chemical science 20180611 26

Described herein is a novel, useful, visible light-promoted ring-opening functionalization of unstrained cycloalkanols. Upon scission of an inert cyclic C-C σ-bond, a set of medium- and large-sized rings are readily brominated under mild reaction conditions to afford the corresponding distal bromo-substituted alkyl ketones that are hard to synthesize otherwise. The products are versatile building blocks, which are easily converted to other valuable molecules in one-step operation. This protocol ...[more]

PMID: 30079191

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