Catalyst-dependent chemoselective insertion of diazoalkanes into the N-H/C-H/O-H/C-O bonds of 2-hydroxybenzothiazoles

Lvnan Jin; Xuan Zhou; Yunbo Zhao; Jing Guo; Douglas W Stephan

doi:10.1039/d2ob01048h

Catalyst-dependent chemoselective insertion of diazoalkanes into the N-H/C-H/O-H/C-O bonds of 2-hydroxybenzothiazoles

Org Biomol Chem. 2022 Oct 12;20(39):7781-7786. doi: 10.1039/d2ob01048h.

Authors

Lvnan Jin¹, Xuan Zhou¹, Yunbo Zhao¹, Jing Guo¹, Douglas W Stephan²

Affiliations

¹ Institute of Drug Discovery Technology, Ningbo University, Ningbo, Zhejiang, 315211, China. guojing@nbu.edu.cn.
² Department of Chemistry, University of Toronto, 80 St George Street, Toronto, Ontario M5S 3H6, Canada. dstephan@chem.utoronto.ca.

PMID: 35792628
DOI: 10.1039/d2ob01048h

Abstract

The control of chemoselective insertions of diazoalkanes into 2-hydroxybenzothiazoles is challenging. Herein, the chemoselective N-H, O-H, C-O or C-H bond insertions of diazoalkanes into 2-hydroxybenzothiazoles are achieved using B(C₆F₅)₃, Rh₂(OAc)₄ or TfOH as the catalyst. This affords routes to 54 benzothiazole derivatives. These protocols are scalable and demonstrate the complementary nature of Lewis acid, transition metal and Brønsted acid catalyses.

Publication types

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

MeSH terms

Benzothiazoles*
Catalysis
Lewis Acids*

Substances

Benzothiazoles
Lewis Acids