Iridium-catalyzed ortho-selective carbon-hydrogen amidation of benzamides with sulfonyl azides in ionic liquid

Lin-Yu Jiao; Zi-Hui Ning; Qian Hong; Xin-Hua Peng; Xiao-Mei Yin; Shanshan Liu; Huiyong Chen; Zhuo Li; Ming Sun; Xiao-Xun Ma

doi:10.1039/d0ra05527a

Iridium-catalyzed ortho-selective carbon-hydrogen amidation of benzamides with sulfonyl azides in ionic liquid

RSC Adv. 2020 Aug 11;10(50):29712-29722. doi: 10.1039/d0ra05527a. eCollection 2020 Aug 10.

Authors

Lin-Yu Jiao^{1

2}, Zi-Hui Ning¹, Qian Hong¹, Xin-Hua Peng¹, Xiao-Mei Yin¹, Shanshan Liu³, Huiyong Chen^{1

2}, Zhuo Li^{1

2}, Ming Sun^{1

2}, Xiao-Xun Ma^{1

2}

Affiliations

¹ School of Chemical Engineering, Northwest University Xi'an Shaanxi 710069 P. R. China lyjiao@nwu.edu.cn.
² International Scientific and Technological Cooperation Base for Clean Utilization of Hydrocarbon Resources, Chemical Engineering Research Center of the Ministry of Education for Advance Use Technology of Shanbei Energy, Shaanxi Research Center of Engineering Technology for Clean Coal Conversion, Collaborative Innovation Center for Development of Energy and Chemical Industry in Northern Shaanxi, Northwest University Xi'an Shaanxi 710069 P. R. China.
³ Shaanxi Key Laboratory of Chemical Additives for Industry, College of Chemistry and Chemical Engineering, Shaanxi University of Science and Technology Xi'an Shaanxi 710021 P. R. China shanshanliu@sust.edu.cn.

Abstract

An efficient and convenient iridium(iii) catalyzed ortho-C-H bond amidation of weakly coordinating benzamides treated with readily available sulfonyl azides as the amino source has been described. In this transformation, ionic liquids represents an ideal reaction medium, giving rise to a broad range of amidation products under mild conditions in the open air. This protocol offers moderate to excellent chemical yields, exclusive regioselectivities, and good functional group tolerance.