Transformation of brucine into trifluoromethyl neobrucine using the homoleptic nickel catalyst [Ni(CF3)4]2
Shreiber, Scott T. 1Puchall, Gabriella I. 1Vicic, David A.1
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作者信息
1. Lehigh Univ
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Abstract
The homoleptic trifluoromethyl nickel complex [Ni(CF3)4]2- catalyzes a stereoselective trifluoromethylation of brucine with Umemoto II reagent. The trifluoromethylation process proceeds with concomitant isomerization of its alkenyl double bond leading to a trifluoromethylated neobrucine-like derivative. A minor difunctionalization product was also detected from the reaction mixture, consistent with a radical addition process that is occurring in parallel. Stoichiometric reactions between the nickel(II) catalyst precursor and brucine led to no reaction. However, a stochiometric reaction with a high-valent nickel(IV) complex formed trifluoromethylated neobrucine, implicating its intermediacy. (c) 2022 Elsevier Ltd. All rights reserved.
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Elsevier