1. Recent Advances in Ring‐Opening Functionalization of Cycloalkanols by C–C σ‐Bond Cleavage.
- Author
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Wu, Xinxin and Zhu, Chen
- Subjects
- *
RING-opening reactions , *ALCOHOLS (Chemical class) , *CARBON-carbon bonds , *KETONES , *POLYCYCLIC aromatic hydrocarbons , *CYCLOBUTANOLS - Abstract
Abstract: Cycloalkanols 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. [ABSTRACT FROM AUTHOR]
- Published
- 2018
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