Metal-free oxidative para-acylation of unprotected anilines with N-heteroarylmethanes,Organic & Biomolecular Chemistry

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Metal-free oxidative para-acylation of unprotected anilines with N-heteroarylmethanes
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2017-10-25 00:00:00 , DOI: 10.1039/c7ob02490h
Min Liu _{1,

2,

3,

4,

5} , Xue Chen _{1,

2,

3,

4,

5} , Tieqiao Chen _{1,

2,

3,

4,

5} , Qing Xu _{5,

6,

7,

8} , Shuang-Feng Yin _{1,

2,

3,

4,

5}

Affiliation

A selective oxidative para-acylation of unprotected anilines with methyl groups in N-heteroarylmethanes was achieved. This transformation proceeds under mild metal-free reaction conditions to produce the corresponding valuable diarylmethanones in good to high yields, featuring high site-selectivity, high functional-group-tolerance, gram-scale synthesis and easy product-derivation. Preliminary mechanistic studies revealed that the present oxidative para-acylation would take place via a Friedel–Crafts-type process of in situ imines and the steric hindrance might be the key issue for the high regio-selectivity.

中文翻译：

未保护的苯胺与N-杂芳基甲烷的无金属氧化对乙酰化

在N-杂芳基甲烷中实现了未保护的苯胺与甲基的选择性氧化对酰化。该转化在温和的无金属反应条件下进行，以高到高收率生产相应的有价值的二芳基亚甲基，具有高的位点选择性，高的官能团耐受性，克级合成和易于衍生的特点。初步的机理研究表明，目前的氧化对酰化反应将通过原位亚胺的Friedel-Crafts型过程进行，并且位阻可能是区域选择性高的关键问题。

更新日期：2017-11-14

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