A novel metal-catalyzed strategy to facilitate the synthesis of terpene amines by a homogeneous pathway is reported. Combining the synergy between 3d and 4d transition metals with glycerol, acting as a boosting solvent, leads to an efficient and selective process for the four-component hydroaminomethylation reaction.
报道了一种新的金属催化策略,通过均相途径促进萜胺的合成。将 3d 和 4d 过渡金属与甘油之间的协同作用相结合,作为增强溶剂,可实现四组分氢氨甲基化反应的高效和选择性过程。
An efficient method for the transformation of naturally occurring monoterpenes into amines through rhodium-catalyzed hydroaminomethylation
作者:Daniela S. Melo、Schubert S. Pereira-Júnior、Eduardo N. dos Santos
DOI:10.1016/j.apcata.2011.10.021
日期:2012.1
The hydroaminomethylation (hydroformylation/reductive amination) of the naturally occurring monoterpenes, i.e., limonene, camphene, and beta-pinene, was studied having as condensation counterparts the amines di-n-butylamine, morpholine or n-butylamine. Moderate to good yields (75-94%) were obtained employing [Rh(cod)(mu-OMe)](2) as pre-catalyst in the presence or not of triphenylphosphine or tribenzylphosphine as ancillaries in toluene, at 100 degrees C and 60 bar of an equimolar mixture of carbon monoxide and hydrogen. Some of the hydroaminomethylation products derived from limonene have biological activity and the products derived from camphene and beta-pinene are new. (C) 2011 Elsevier BM. All rights reserved.