American Chemical Society
jo3c01294_si_001.pdf (8.86 MB)

Accessing para-Alkylphenols via Iridium-Catalyzed Site-Specific Deoxygenation of Alcohols

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journal contribution
posted on 2023-08-18, 17:34 authored by Jing Wang, Tingting Wang, Hongguang Du, Ning Chen, Jiaxi Xu, Zhanhui Yang
An iridium-catalyzed and phenol-directed deoxygenation of benzylic alcohols comes as an alternative access to 4-alkylphenols, featuring low catalyst loading (S/C up to 20,000, TOF up to 12,400 h–1), high functionality compatibility, and excellent site-selectivity. The applications in late-stage modification of steroids and gram-scale total synthesis of a Gastrodia elata extract are highlighted. Mechanistically, the intermediacy of quinone methide controls the site-selectivity, and the formation of iridium hydride serves as the rate-limiting step.