化学
二苯甲酮
部分
电泳剂
三氟乙酸酐
位阻效应
苯乙酮
有机化学
硼
催化作用
酮
药物化学
作者
Maxim A. Novikov,Angelina Yu. Bobrova,Igor A. Mezentsev,Michael G. Medvedev,Yury V. Tomilov
标识
DOI:10.1021/acs.joc.9b03445
摘要
Efficient routes toward activation of gem-chlorofluorocyclopropane-derived (2-fluoroallyl)boronates for allylboration of various ketones including functionalized and low-reactive ones were developed. Increasing the boron electrophilicity by the transformation of a boronate moiety into a borinic ester with nBuLi/trifluoroacetic anhydride (TFAA) makes (2-fluoroallyl)boration of acetyl arenes/hetarenes and aliphatic ketones possible with high diastereoselectivity. For low-reactive or sterically hindered ketones (e.g., benzophenone, adamantanone), "CuF"-based catalysts were developed: (NHC)CuF·HF and (NHC)CuOTf in the presence of an excess of KHF2 (NHC = IPr, SIPr, IPrCl).
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