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Media type:
E-Article
Title:
Recent Advances in Ring‐Opening Functionalization of Cycloalkanols by C–C σ‐Bond Cleavage
Contributor:
Wu, Xinxin;
Zhu, Chen
Published:
Wiley, 2018
Published in:
The Chemical Record, 18 (2018) 6, Seite 587-598
Language:
English
DOI:
10.1002/tcr.201700090
ISSN:
1528-0691;
1527-8999
Origination:
Footnote:
Description:
AbstractCycloalkanols prove to be privileged precursors for the synthesis of distally substituted alkyl ketones and polycyclic aromatic hydrocarbons (PAHs) by virtue of cleavage of their cyclic C−C bonds. Direct functionalization of cyclobutanols to build up other chemical bonds (e. g., C−F, C−Cl, C−Br, C−N, C−S, C−Se, C−C, etc.) has been achieved by using the ring‐opening strategy. Mechanistically, the C−C cleavage of cyclobutanols can be involved in two pathways: (a) transition‐metal catalyzed β‐carbon elimination; (b) radical‐mediated ‘radical clock’‐type ring opening. The recent advances of our group for the ring‐opening functionalization of tertiary cycloalkanols are described in this account.