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“大体积而灵活”的α-二亚胺钯催化还原 Heck 交叉偶联反应:在空气中烯烃的高反马氏选择性氢芳基化。

"Bulky-Yet-Flexible" α-Diimine Palladium-Catalyzed Reductive Heck Cross-Coupling: Highly Anti-Markovnikov-Selective Hydroarylation of Alkene in Air.

机构信息

School of Chemistry and Chemical Engineering, Guangdong Cosmetics Engineering & Technology Research Center, Guangdong Pharmaceutical University, Zhongshan, Guangdong 528458, China.

出版信息

J Org Chem. 2020 Sep 18;85(18):11750-11765. doi: 10.1021/acs.joc.0c01509. Epub 2020 Aug 31.

DOI:10.1021/acs.joc.0c01509
PMID:32808522
Abstract

To pursue a highly regioselective and efficient reductive Heck reaction, a series of moisture- and air-stable α-diimine palladium precatalysts were rationally designed, readily synthesized, and fully characterized. The relationship between the structures of the palladium complexes and the catalytic properties was investigated. It was revealed that the"bulky-yet-flexible"palladium complexes allowed highly anti-Markovnikov-selective hydroarylation of alkenes with (hetero)aryl bromides under aerobic conditions. Further synthetic application of the present protocol could provide rapid and straightforward access to functional and biologically active molecules.

摘要

为了追求高区域选择性和高效的还原 Heck 反应,设计、简便合成并充分表征了一系列对湿度和空气稳定的α-二亚胺钯前催化剂。研究了钯配合物的结构与催化性能之间的关系。结果表明,“大而灵活”的钯配合物允许在有氧条件下,高反马氏选择性地对烯烃与(杂)芳基溴化物进行氢芳基化反应。本方法的进一步合成应用可以快速、直接地获得功能和生物活性分子。

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