钯催化共轭烯炔酮与有机硼酸的氧化交叉偶联反应

Palladium-Catalyzed Oxidative Cross-Coupling of Conjugated Enynones with Organoboronic Acids.

作者信息

Xia Ying, Ge Rui, Chen Li, Liu Zhen, Xiao Qing, Zhang Yan, Wang Jianbo

机构信息

†Beijing National Laboratory of Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, China.

‡State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China.

出版信息

J Org Chem. 2015 Aug 21;80(16):7856-64. doi: 10.1021/acs.joc.5b01350. Epub 2015 Aug 4.

DOI:10.1021/acs.joc.5b01350

PMID:26219829

Abstract

A palladium-catalyzed oxidative cross-coupling reaction of conjugated enynones with organoboronic acids is developed. This reaction provides an efficient methodology for the synthesis of functionalized furan derivatives, including 2-alkenylfurans and furan-substituted 1,3-dienes. Palladium-carbene migratory insertion is proposed as the key step in these transformations. Notably, the β-hydride elimination process occurs in a stereoselective manner, resulting in the formation of double bonds with high (E)-selectivity.

摘要

开发了一种钯催化的共轭烯炔酮与有机硼酸的氧化交叉偶联反应。该反应为合成功能化呋喃衍生物提供了一种有效的方法，包括2-烯基呋喃和呋喃取代的1,3-二烯。钯-卡宾迁移插入被认为是这些转化的关键步骤。值得注意的是，β-氢消除过程以立体选择性方式发生，导致形成具有高（E）-选择性的双键。