期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 88, 期 17, 页码 12572-12584出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.3c01294
关键词
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An iridium-catalyzed and phenol-directed deoxygenation method is described for the synthesis of 4-alkylphenols, which offers low catalyst loading, 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 also highlighted. Mechanistically, the interemediacy of quinone methide controls the site-selectivity, and the formation of iridium hydride serves as the rate-limiting step.
An iridium-catalyzed and phenol-directed deoxygenationof benzylicalcohols comes as an alternative access to 4-alkylphenols, featuringlow catalyst loading (S/C up to20,000, TOF up to 12,400 h(-1)), high functionalitycompatibility, and excellent site-selectivity. The applications inlate-stage modification of steroids and gram-scale total synthesisof a Gastrodia elata extract are highlighted.Mechanistically, the intermediacy of quinone methide controls thesite-selectivity, and the formation of iridium hydride serves as therate-limiting step.
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