TBHP/Et3N-Promoted Chemoselective Formylation and Peroxidation of Pyrrolo[2,1-a]isoquinolines
Xiang Huang1,2, Jing Zhou1, Shu-Chen Pei2
1Laboratory of Asymmetric Synthesis, College of Chemistry and Environmental Engineering, Chongqing University of Arts and Sciences, 319 Honghe Avenue, Yongchuan, Chongqing 402160, P. R. China.
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.
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