TBHP/Et3N-Promoted Chemoselective Formylation and Peroxidation of Pyrrolo[2,1- a]isoquinolines

Xiang Huang; Jing Zhou; Shu-Chen Pei; Hai-Lei Cui

doi:10.1021/acs.joc.4c00321

TBHP/Et₃N-Promoted Chemoselective Formylation and Peroxidation of Pyrrolo[2,1- a]isoquinolines

J Org Chem. 2024 May 3;89(9):6353-6363. doi: 10.1021/acs.joc.4c00321. Epub 2024 Apr 16.

Authors

Xiang Huang^{1

2}, Jing Zhou¹, Shu-Chen Pei², Hai-Lei Cui¹

Affiliations

¹ Laboratory of Asymmetric Synthesis, College of Chemistry and Environmental Engineering, Chongqing University of Arts and Sciences, 319 Honghe Avenue, Yongchuan, Chongqing 402160, P. R. China.
² School of Chemistry and Chemical Engineering, Chongqing University of Science and Technology, Chongqing 401331, P. R. China.

PMID: 38625867
DOI: 10.1021/acs.joc.4c00321

Abstract

An efficient formylation of pyrrolo[2,1-a]isoquinoline derivatives has been reached by the use of TBHP (tBuOOH) and Et₃N as the mediator. In this strategy, CHO and CDO can be readily incorporated into heteroarenes by the utilization of CHCl₃ and CDCl₃ as the carbonyl sources. Interestingly, a solvent-controlled chemoselectivity was observed. The use of PhCl as a solvent resulted in dearomatization and peroxidation of pyrrolo[2,1-a]isoquinolines, delivering functionalized peroxides in 53-64% yields.