Radical-Mediated α-tert-Alkylation of Aldehydes by Consecutive 1,4- and 1,3-(Benzo)thiazolyl Migrations
Chen Zhu and Xiao-Song Xue describe consecutive 1,4- and 1,3-(benzo)thiazolyl migrations to alkylate aldehydes.
The direct alkylation of aliphatic aldehydes in α-position represents a common strategy for the preparation of complex functionalized aldehydes, which are present in numerous natural products and functional molecules. The precedents are mainly limited to the incorporation of primary and secondary alkyl groups by electrophilic alkylation, while the tert-alkylation of aldehydes remains challenging due to steric hindrance and halide elimination often occurring with tertiary alkyl halides. A recent article from the groups of Professor Chen Zhu at Shanghai Jiao Tong University and Professor Xiao-Song Xue at Shanghai Institute of Organic Chemistry (both P. R. of China) describes a novel radical cascade for the elusive tert-alkylation of aldehydes, leading to structurally diverse aldehydes.
Read the full article Radical-Mediated α-tert-Alkylation of Aldehydes by Consecutive 1,4- and 1,3-(Benzo)thiazolyl Migrations
