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

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-s...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2018-07, Vol.9 (26), p.5805-5809
Main Authors: Wang, Dongping, Mao, Jincheng, Zhu, Chen
Format: Article
Language:English
Subjects:
Bromination
Chemistry
Cleavage
Ketones
Molecular chains
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Summary: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.
ISSN:2041-6520
2041-6539
DOI:10.1039/c8sc01763h