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钯催化的含炔基苯酚基联芳烃的级联环化/去芳构化/芳基化反应:一种用于合成多官能化螺环己二烯酮的方法。

Palladium-Catalyzed Cascade Cyclization/Dearomatization/Arylation of Alkyne-Containing Phenol-Based Biaryls with Aryl Halides: An Entry to Diversely Functionalized Spirocyclohexadienones.

机构信息

Inner Mongolia Key Laboratory of Fine Organic Synthesis, Department of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot 010021, China.

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.

出版信息

J Org Chem. 2020 May 15;85(10):6687-6696. doi: 10.1021/acs.joc.0c00710. Epub 2020 May 7.

DOI:10.1021/acs.joc.0c00710
PMID:32345018
Abstract

A convenient method for the synthesis of aryl-functionalized spirocyclohexadienone scaffolds from alkyne-containing phenol-based biaryls with aryl halides via palladium-catalyzed cyclization/dearomatization/arylation is developed. The approach provides a series of spirocyclohexadienone molecules in moderate to high yields. The reaction occurs chemoselectively through dearomative C-arylation rather than common O-arylation of phenols.

摘要

发展了一种钯催化的环化/去芳构化/芳基化反应,从含炔基的酚基联苯和芳基卤化物方便地合成芳基功能化的螺环环己二烯酮骨架。该方法以中等至高产率提供了一系列螺环环己二烯酮分子。反应通过去芳构化的 C-芳基化而不是酚的常见 O-芳基化进行化学选择性。

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