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镍催化的多米诺 Heck 环化/Suzuki 偶联反应合成 3,3-二取代氧吲哚。

Nickel-Catalyzed Domino Heck Cyclization/Suzuki Coupling for the Synthesis of 3,3-Disubstituted Oxindoles.

机构信息

The Institute for Advanced Studies, Wuhan University , 299 Bayi Road, Wuchang District, Wuhan, Hubei 430072, P. R. China.

出版信息

Org Lett. 2018 Feb 16;20(4):921-924. doi: 10.1021/acs.orglett.7b03713. Epub 2018 Jan 26.

Abstract

The first nickel-catalyzed domino Heck cyclization/Suzuki coupling reaction for the synthesis of 3,3-disubstituted oxindoles bearing quaternary all-carbon centers is reported. A wide range of electrophiles, such as aryl iodides, bromides, triflates, and chlorides, are all compatible with the reaction conditions. Moreover, cheap aryl esters, which undergo catalytic C-O bond cleavage, could also be employed as electrophiles. The approach shows good yields and broad scope, complementing a more practical and sustainable alternative to the conventional palladium-based analogues.

摘要

首次报道了镍催化的串联 Heck 环化/Suzuki 偶联反应,用于合成具有季碳中心的 3,3-二取代氧吲哚。该反应条件兼容各种亲电试剂,如芳基碘化物、溴化物、三氟甲磺酸酯和氯化物。此外,廉价的芳基酯类化合物(可发生催化 C-O 键断裂)也可用作亲电试剂。该方法具有良好的收率和广泛的适用范围,为传统钯基类似物提供了更实用、更可持续的替代方案。

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