AlCl3-Meditated CHF2 Transfer and Cyclocondensation of Difluoromethoxy Functionalized o-Phenylenediamines to Access N-Substituted Benzimidazoles

被引：3

作者：

Vinayagam, Vinothkumar ^{[1
]}

Karre, Satish Kumar ^{[1
]}

Kasu, Sreenivasa Reddy ^{[1
]}

Srinath, Ravuri ^{[1
]}

Bathula, Hema Sundar Naveen Babu ^{[1
]}

Sadhukhan, Subir Kumar ^{[1
]}

机构：

[1] Curia India Pvt Ltd, Hyderabad 500078, India

来源：

ORGANIC LETTERS | 2022年

关键词：

ACTIVATION; NUCLEOPHILE; REACTIVITY; DIHYDROGEN; AMIDATION; STABILITY; CHEMISTRY; CLEAVAGE; METHANOL; ACID;

D O I：

10.1021/acs.orglett.2c02231

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we report for the first time a transition-metal-free frustrated Lewis pair (FLP) catalyzed CHF2 group migration from an oxygen atom to the neighboring nitrogen atom, which led to the synthesis of N-substituted benzimidazoles at room temperature with excellent yields, broad functional group tolerance, and a short reaction time. The oxygen-attached difluoromethane acted as a C1 source in the synthesis of N-substituted benzimidazoles in the presence of AlCl3 by cleaving one C-O bond and two C-F bonds, resulting in formation of two new C-N bonds.

引用

收藏

页码：6142 / 6147

页数：6

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