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气氛控制下钯催化的2-碘代联苯与α-氧代羧酸的发散性脱羧环化反应

Atmosphere-Controlled Palladium-Catalyzed Divergent Decarboxylative Cyclization of 2-Iodobiphenyls and α-Oxocarboxylic Acids.

作者信息

Zhou Liwei, Sun Mingjie, Zhou Fengru, Deng Guobo, Yang Yuan, Liang Yun

机构信息

National & Local Joint Engineering Laboratory for New Petro-chemical Materials and Fine Utilization of Resources, Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research, Ministry of Education, Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, Hunan Normal University, Changsha, Hunan 410081, People's Republic of China.

出版信息

Org Lett. 2021 Sep 17;23(18):7150-7155. doi: 10.1021/acs.orglett.1c02559. Epub 2021 Aug 31.

DOI:10.1021/acs.orglett.1c02559
PMID:34463519
Abstract

A novel palladium-catalyzed divergent decarboxylative cyclization of 2-iodobiphenyls and α-oxocarboxylic acids utilizing the atmosphere as a controlled switch is reported. Under the protection of a nitrogen atmosphere, tribenzotropones are synthesized by a [4 + 3] decarboxylative cyclization. Employing a palladium/O system enables a [4 + 2] decarboxylative cyclization to assemble triphenylenes. Notably, preliminary mechanistic studies indicate that the formation of triphenylenes involves a double decarboxylation.

摘要

报道了一种利用大气作为可控开关的新型钯催化的2-碘联苯与α-氧代羧酸的发散性脱羧环化反应。在氮气气氛保护下,通过[4 + 3]脱羧环化反应合成了三苯并环庚三烯。采用钯/氧体系可实现[4 + 2]脱羧环化反应以组装三亚苯基。值得注意的是,初步机理研究表明三亚苯基的形成涉及双重脱羧反应。

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