Cobalt-Catalyzed Deprotection of Allyl Carboxylic Esters Induced by Hydrogen Atom Transfer

Nan Li; Yizhen Gui; Mengqi Chu; Mengdi You; Xiaohan Qiu; Hejia Liu; Shiang Wang; Meng Deng; Baoming Ji

doi:10.1021/acs.orglett.1c03185

Cobalt-Catalyzed Deprotection of Allyl Carboxylic Esters Induced by Hydrogen Atom Transfer

Org Lett. 2021 Nov 5;23(21):8460-8464. doi: 10.1021/acs.orglett.1c03185. Epub 2021 Oct 20.

Authors

Nan Li¹, Yizhen Gui¹, Mengqi Chu¹, Mengdi You¹, Xiaohan Qiu¹, Hejia Liu¹, Shiang Wang¹, Meng Deng², Baoming Ji¹

Affiliations

¹ Henan Key Laboratory of Function-Oriented Porous Materials, College of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang, Henan 471934, People's Republic of China.
² Luoyang Key Laboratory of Organic Functional Molecules, College of Food and Drug, Luoyang Normal University, Luoyang, Henan 471934, People's Republic of China.

PMID: 34670095
DOI: 10.1021/acs.orglett.1c03185

Abstract

A brief, efficient method has been developed for the removal of the allyl protecting group from allyl carboxylic esters using a Co(II)/TBHP/(Me₂SiH)₂O catalytic system. This facile strategy displays excellent chemoselectivity, functional group tolerance, and high yields. This transformation probably occurs through the hydrogen atom transfer process, and a Co(III)-six-membered cyclic intermediate is recommended.