Intermolecular Reductive Heck Reaction of Unactivated AliphaticAlkenes with Organohalides

Kewang Zheng,^aGuanlin Xiao,^aTao Guo,^aYalan Ding,^aChengdong Wang,^aTeck-Peng Loh,^ab*and Xiaojin Wu^a*

^aInstitute of Advanced Synthesis, School of Chemistry and Molecular Engineering,Nanjing Tech University, Nanjing 211816, China

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

Abstract:A general intermolecular reductive Heck reaction of organohalides with both terminal and internal unactivatedaliphatic alkenes has been first realized in high yield with completeanti-Markovnikov selectivity. The challenging vinyl bromides, arylchlorides, and polysubstituted internal alkenes were first applied. More than 100 remote carbofunctionalized alkyl carboxylic acidderivatives were rapidly synthesized from easily accessible starting materials. The synthesis of drug molecules has furtherdemonstrated the wide synthetic utility of this scalable strategy. Preliminary mechanistic studies are consistent with the proposedcatalytic cycle.

Org. Lett.2020,DOI:org/10.1021/acs.orglett.9b04474（影响因子：6.555）

文章链接：https://doi.org/10.1021/acs.orglett.9b04474