Iridium-Catalyzed ortho-C(sp2)-H Amidation of Benzaldehydes with Organic Azides

Delong Mu; Xinmou Wang; Gong Chen; Gang He

doi:10.1021/acs.joc.7b00531

Iridium-Catalyzed ortho-C(sp²)-H Amidation of Benzaldehydes with Organic Azides

J Org Chem. 2017 Apr 21;82(8):4497-4503. doi: 10.1021/acs.joc.7b00531. Epub 2017 Apr 12.

Authors

Delong Mu^{1

2}, Xinmou Wang^{1

2}, Gong Chen^{1

2

3}, Gang He^{1

2}

Affiliations

¹ State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University , Tianjin 300071, China.
² Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) , Tianjin 300071, China.
³ Department of Chemistry, The Pennsylvania State University , University Park, Pennsylvania 16802, United States.

PMID: 28383264
DOI: 10.1021/acs.joc.7b00531

Abstract

An iridium-catalyzed ortho-C(sp²)-H amidation reaction of benzaldehydes with organic azides has been developed. A catalytic amount of 3,5-di(trifluoromethyl)aniline was used to promote the Ir-catalyzed directed C-H amination reaction through a transient aldimine intermediate. This reaction tolerates a broad scope of benzaldehyde substrates and works well with a range of aryl- and alkylsulfonyl azides.

Publication types

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