Palladium-catalyzed regiocontrollable reductive Heck reaction of unactivated aliphatic alkenes

• Main Authors: Wang, Chengdong, Xiao, Guanlin, Guo, Tao, Ding, Yalan, Wu, Xiaojin, Loh, Teck-Peng
• Other Authors: School of Physical and Mathematical Sciences
• Format: Article
• Language: English
• Published: 2020
• Subjects: Engineering::Chemical engineering; Hydrocarbons; Anions
• Online Access: https://hdl.handle.net/10356/139270
• Institution: Nanyang Technological University

A general Pd-catalyzed intermolecular reductive Heck reaction of both terminal and internal unactivated aliphatic alkenes has been first developed. This method affords γ- and δ-arylated alkyl carboxylic acid derivatives in high yields with complete anti-Markovnikov selectivity. Notably, the coupling process is stereoretentive for the alkyl chain. Mechanistically, alkyl palladacycle intermediates stabilized by directing group and ligand, hydride species multigenerated from PS/TFA reductant, are two key factors that successfully promote the reaction and regioselectivity.