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Issue 26, 2018
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Visible light-promoted ring-opening functionalization of unstrained cycloalkanols via inert C–C bond scission

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Abstract

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 is also applicable to the unprecedented ring-opening cyanation and alkynylation of unstrained cycloalkanols.

Graphical abstract: Visible light-promoted ring-opening functionalization of unstrained cycloalkanols via inert C–C bond scission

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Supplementary files

Article information


Submitted
18 Apr 2018
Accepted
08 Jun 2018
First published
11 Jun 2018

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2018,9, 5805-5809
Article type
Edge Article

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

D. Wang, J. Mao and C. Zhu, Chem. Sci., 2018, 9, 5805
DOI: 10.1039/C8SC01763H

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