Palladium-Catalyzed Regiocontrollable Reductive Heck Reaction of Unactivated Aliphatic Alkenes

Chengdong Wang,^aGuanlin Xiao,^aTao Guo,^aYalan Ding,^aXiaojin Wu^*,aand Teck-Peng Loh*^,ab

^aInstitute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Jiangsu National Synergetic Innovation Center for Advanced Materials, Nanjing Tech University, Nanjing 211816, P. R. China

^bDivision of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637616

Abstract:A general Pd-catalyzed intermolecular reductive Heck reaction of both terminal and internal unactivated aliphatic alkenes has been firstly 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 multi-generated from PS/TFA reductant, are two key factors that successfully promote the reaction and regioselectivity.

JACS.2018,DOI: 10.1021/jacs.8b03619(2017年影响因子: 13.858，第一作者为硕士研究生王成东).

论文链接：https://pubs.acs.org/doi/pdf/10.1021/jacs.8b03619

（转载自：http://ias.njtech.edu.cn/ch/view.asp?id=1802&class=165）

（审核：杨文忠）