Copper(I)-Catalyzed Formal [4 + 2] Cyclocondensation of ortho-Hydroxybenzyl Alcohol, Aromatic Terminal Alkynes, and Sulfonyl Azides: An Alternative Approach to 2-Sulfonyliminocoumarins

Author:

Khan Dost Muhammad1,Lv Jiaying1,Hua Ruimao1ORCID

Affiliation:

1. Key Laboratory of Organic Optoelectronics & Molecular Engineering of Ministry of Education, Department of Chemistry, Tsinghua University, Beijing 100084, China

Abstract

In this paper, an alternative and efficient copper(I)-catalyzed synthesis of 2-sulfonyliminocoumarins is developed through a three-component reaction of ortho-hydroxybenzyl alcohol, alkynes, and p-toluenesulfonyl azide. The proposed route for access to the 2-iminocoumarin ring involves a [4 + 2] hetero-Diels-Alder reaction between ortho-quinone methide and ketenimine intermediates generated in situ.

Funder

National Natural Science Foundation of China

Publisher

MDPI AG

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