Catalyst-free, direct electrochemical synthesis of annulated medium-sized lactams through C–C bond cleavage,Green Chemistry

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Catalyst-free, direct electrochemical synthesis of annulated medium-sized lactams through C–C bond cleavage
Green Chemistry ( IF 9.3 ) Pub Date : 2019/12/11 , DOI: 10.1039/c9gc03901e
Zhongnan Xu _{1,

2,

3,

4,

5} , Zhixing Huang _{1,

2,

3,

4,

5} , Yueheng Li _{1,

2,

3,

4,

5} , Rositha Kuniyil _{6,

7,

8,

9} , Chao Zhang _{1,

2,

3,

4,

5} , Lutz Ackermann _{6,

7,

8,

9} , Zhixiong Ruan _{1,

2,

3,

4,

5}

Affiliation

A catalyst-free, direct electrochemical synthesis of synthetically challenging medium-sized lactams through C–C bond cleavage has been developed. In contrast to previous typical amidyl radical cyclization, this electrosynthetic approach enabled step-economical ring expansion through a unique remote amidyl migration under mild, metal- and external-oxidant-free conditions in a simple undivided cell. The strategy features unparalleled broad substrate scope with all ring sizes of (hetero)aryl-fused 8–11-membered rings and hetero atom-tethered rings, high yields, and good functional group tolerance. Our experimental and computational findings provided strong support for a SET-based reaction manifold.

中文翻译：

通过CC键断裂，无催化剂的中型内酰胺环的直接电化学合成

已经开发出了一种无催化剂的，通过C-C键断裂合成具有挑战性的中等尺寸内酰胺的直接电化学合成方法。与以前的典型酰胺基自由基环化反应相反，这种电合成方法通过在简单，无分隔的温和，无金属和外部氧化剂条件下，通过独特的远程酰胺基迁移，实现了经济实惠的环扩环。该策略具有无与伦比的广泛底物范围，具有（杂）芳基稠合的8-11元环和杂原子链环的所有环尺寸，高收率和良好的官能团耐受性。我们的实验和计算结果为基于SET的反应歧管提供了有力的支持。

更新日期：2020-02-24

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