Harnessing Applied Potential: Selective β-Hydrocarboxylation of Substituted Olefins
作者:Anas Alkayal、Volodymyr Tabas、Stephanie Montanaro、Iain A. Wright、Andrei V. Malkov、Benjamin R. Buckley
DOI:10.1021/jacs.9b13305
日期:2020.1.29
The construction of carboxylic acid compounds in a selective fashion from low value materials such as alkenes remains a long-standing challenge to synthetic chemists. In particular, β-addition to styrenes is underdeveloped. Herein we report a new electrosynthetic approach to the selective hydrocarboxylation of alkenes that overcomes the limitations of current transition metal and photochemical approaches
A palladium-catalyzed allylic C−H oxidative allylation of N-tosylhydrazones to synthesize skipped 1,4-dienes is demonstrated. This direct allylic alkylation reaction has excellent site selectivity, tolerates a wide range of functional groups, and affords 1,4-dienes in moderate to good yield. Moreover, this olefination method allows the regio- and stereoselective synthesis of 1,4-dienes containing a