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钯催化的烯丙基芳基卤化物与 -溴代苯甲酸的级联环化:获得多种稠合的吲哚并[2,1-]异喹啉。

Palladium-Catalyzed Cascade Cyclization of Alkene-Tethered Aryl Halides with -Bromobenzoic Acids: Access to Diverse Fused Indolo[2,1-]isoquinolines.

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 , China.

出版信息

Org Lett. 2019 Sep 20;21(18):7284-7288. doi: 10.1021/acs.orglett.9b02541. Epub 2019 Sep 10.

Abstract

A novel palladium-catalyzed cascade cyclization of alkene-tethered aryl halides with -bromobenzoic acids is described, which provides an efficient avenue for building various fused hexacyclic scaffolds containing indolo[2,1-]isoquinoline in moderate to excellent yield. The method enables the construction of three C-C bonds through an intramolecular carbopalladation, C-H activation, and a decarboxylation sequence. Furthermore, dihydrocyclohepta[]naphthalene-fused indolo[2,1-]isoquinolines can be synthesized in moderate yield by constructing a seven-membered ring.

摘要

本文描述了一种新型钯催化的烯丙基芳基卤化物与 -溴苯甲酸的级联环化反应,为构建各种含有吲哚并[2,1-]异喹啉的稠合六元环骨架提供了一种有效途径,产率中等至优秀。该方法通过分子内碳钯化、C-H 活化和脱羧反应序列实现了三个 C-C 键的构建。此外,通过构建七元环,中等产率地合成了二氢环庚[]萘并吲哚并[2,1-]异喹啉。

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