Highly efficient one-pot synthesis of N-sulfonylamidines by Cu-catalyzed three-component coupling of sulfonyl azide, alkyne, and amine

Imhyuck Bae; Hoon Han; Sukbok Chang

doi:10.1021/ja0432968

Highly efficient one-pot synthesis of N-sulfonylamidines by Cu-catalyzed three-component coupling of sulfonyl azide, alkyne, and amine

J Am Chem Soc. 2005 Feb 23;127(7):2038-9. doi: 10.1021/ja0432968.

Authors

Imhyuck Bae¹, Hoon Han, Sukbok Chang

Affiliation

¹ Center for Molecular Design and Synthesis, Department of Chemistry and School of Molecular Science (BK21), Korea Advanced Institute of Science and Technology, Daejon 305-701, Republic of Korea.

PMID: 15713069
DOI: 10.1021/ja0432968

Abstract

A highly efficient, mild, practical, and catalytic multicomponent reaction for the synthesis of N-sulfonylamidines has been developed. This reaction has an extremely wide scope with regard to all three coupling components of alkyne, sulfonyl azide, and amine. Two plausible mechanistic pathways involving ketenimine or triazole intermediate are tentatively presented for the copper-catalyzed three-component coupling reactions.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkynes / chemistry*
Amidines / chemical synthesis*
Amidines / chemistry
Amines / chemistry*
Azides / chemistry*
Sulfinic Acids / chemical synthesis*
Sulfinic Acids / chemistry

Substances

Alkynes
Amidines
Amines
Azides
Sulfinic Acids