Palladium-Catalyzedanti-Michael Reductive Heck Reaction ofα,β-Unsaturated Esters

Tao Guo,^aYalan Ding,^aLili Zhou,^aHaiyan Xu,^cTeck-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)

^cSchool of Environmental and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang, Jiangsu 212003, China

Abstract:A general intermolecularanti-Michael reductive Heck reaction ofα,β-unsaturated esters with organobromides has been developed. Most topical classes of aryl, heteroaryl, and vinyl bromides were found to efficiently react with a variety of internal conjugated alkenes. This protocol set up a platform toward diverseα-arylated 1,6-dicarbonyl frameworks found in natural products and drugs, which are still highly challenging targets in traditionalα-arylation protocols because of competitive selectivity of enolation. A removable directing group, gram-scale reaction, and modification of complex molecules have additionally demonstrated that theanti-Michael reductive Heck reaction is a powerful complementary strategy to the classicalα-arylation approaches. Preliminary mechanistic studies are consistent with our proposed mechanistic design.

ACS Catal.2020,DOI:org/10.1021/acscatal.0c02414(影响因子：12.221)

文章链接：https://doi.org/10.1021/acscatal.0c02414