Nickel-catalyzed <i>C</i>-alkylation of thioamide, amides and esters by primary alcohols through a hydrogen autotransfer strategy
Peng Yang, Xiuhua Wang, Yu Ma, Yaxin Sun, Li Zhang, Jieyu Yue, Kaiyue Fu, Jianrong Steve Zhou, Bo Tang
Abstract
A simple catalyst of Ni(OAc)2 and P(t-Bu)3 enables selective C-alkylation of thioacetamides and primary acetamides with alcohols for the first time. Monoalkylation of thioamides, amides and t-butyl esters occurs in excellent yields (>95%). Mechanistic studies reveal that the reaction proceeds via a hydrogen autotransfer pathway.
Topics & Concepts
ThioamideCatalysisPrimary (astronomy)ChemistryAlkylationNickelHydrogenOrganic chemistryCombinatorial chemistryPhysicsAstronomyAsymmetric Hydrogenation and CatalysisCarbon dioxide utilization in catalysisChemical Synthesis and Analysis