CuI-Catalyzed Dearomatization/Peroxidation/Cyclization Cascade of Pyrrole-Tethered Indoles

Xue Sheng; Liu Yang; Jia-Yi Han; Xin Yu; Hai-Lei Cui

doi:10.1021/acs.joc.4c02977

CuI-Catalyzed Dearomatization/Peroxidation/Cyclization Cascade of Pyrrole-Tethered Indoles

J Org Chem. 2025 Mar 14;90(10):3639-3652. doi: 10.1021/acs.joc.4c02977. Epub 2025 Feb 27.

Authors

Xue Sheng¹, Liu Yang¹, Jia-Yi Han¹, Xin Yu¹, Hai-Lei Cui¹

Affiliation

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.

PMID: 40014766
DOI: 10.1021/acs.joc.4c02977

Abstract

A mild CuI-catalyzed dearomatization/peroxidation/cyclization cascade of pyrrole-tethered indoles has been reached, providing peroxide-incorporated indolizino[8,7-b]indole derivatives in acceptable to good yields (46-76%). Dehydrogenated peroxide can be obtained by the use of a FeCl₃/TBHP (tBuOOH)/2,2,2-trifluoroethanol (TFE) system at 50 °C.