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基于铑催化碳氢键官能团化的八元内酰胺合成方法

Rhodium-catalyzed C-H functionalization-based approach to eight-membered lactams.

作者信息

Wu Shangze, Zeng Rong, Fu Chunling, Yu Yihua, Zhang Xue, Ma Shengming

机构信息

Laboratory of Molecular Recognition and Synthesis , Department of Chemistry , Zhejiang University , Hangzhou 310027 , Zhejiang , P. R. China . Email:

Shanghai Key Laboratory of Magnetic Resonance , Department of Physics , East China Normal University , Shanghai 200062 , P. R. China.

出版信息

Chem Sci. 2015 Apr 1;6(4):2275-2285. doi: 10.1039/c5sc00092k. Epub 2015 Feb 5.

Abstract

A Rh(iii) catalyzed formal [4 + 2 + 2] cyclization of -pivaloyloxybenzamides with 1,6-allene-enes by C-H functionalization is reported. The reactions occur at room temperature and are compatible with air and moisture with a tolerance of many synthetically useful functional groups. The follow-up modifications of the products have been demonstrated. After careful mechanistic studies and DFT calculation, a reaction mechanism was proposed.

摘要

报道了一种铑(iii)催化的对新戊酰氧基苯甲酰胺与1,6-联烯通过C-H官能化进行的形式上的[4 + 2 + 2]环化反应。该反应在室温下进行,与空气和水分兼容,对许多具有合成用途的官能团具有耐受性。已证明了产物的后续修饰。经过仔细的机理研究和密度泛函理论计算,提出了一种反应机理。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b1ed/5645731/e37852178c86/c5sc00092k-s1.jpg

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