Recent Advances in Ring ‐Opening Functionalization of Cycloalkanols by C–C σ‐Bond Cleavage

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.

C−C σ‐bond cleavage: 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. The recent advances in the ring‐opening functionalization of tertiary cycloalkanols are summarized in this account.

Source: Contrast Media and Molecular Imaging - February 1, 2018 Category: Radiology Authors: Xinxin Wu, Chen Zhu Tags: Personal Account Source Type: research