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铜催化的炔烃连接的α-溴代羰基化合物与炔烃的环化串联反应:杂多环的一种获得途径。

Copper-Catalyzed Annulation Cascades of Alkyne-Tethered α-Bromocarbonyls with Alkynes: An Access to Heteropolycycles.

机构信息

State Key Laboratory of Chemo/Biosensing and Chemometrics , Hunan University , Changsha 410082 , China.

Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle , Nanchang Hangkong University , Nanchang 330063 , China.

出版信息

Org Lett. 2018 Apr 20;20(8):2129-2132. doi: 10.1021/acs.orglett.8b00236. Epub 2018 Mar 29.

Abstract

We here describe a new Cu-catalyzed annulation cascade of alkyne-tethered α-bromocarbonyls with common alkynes for the synthesis of various heteropolycycle frameworks, including 1 H-benzo[ de]quinolin-2(3 H)-ones, 4 H-dibenzo[ de,g]quinolin-5(6 H)-one, and benzo[ de]chromen-2(3 H)-one, which were constructed with high selectivity. This was achieved by two-component annulation cascades, rather than atom-transfer radical cyclization (ATRC), with alkyne-tethered α-bromocarbonyls for one-step accessing heteropolycycles via C-Br bond split, intramolecular cyclization, intermolecular [4 + 2] annulation, and aryl C(sp)-H functionalization cascades.

摘要

我们在这里描述了一种新的铜催化的炔烃连接的α-溴代羰基与常见炔烃的环化串联反应,用于合成各种杂多环骨架,包括 1 H-苯并[de]喹啉-2(3 H)-酮、4 H-二苯并[de,g]喹啉-5(6 H)-酮和苯并[de]色烯-2(3 H)-酮,这些产物具有很高的选择性。这是通过两步环化串联反应而不是原子转移自由基环化(ATRC)来实现的,炔烃连接的α-溴代羰基通过 C-Br 键断裂、分子内环化、分子间[4+2]环加成和芳基 C(sp)-H 官能化串联反应一步构建杂多环。

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