A manganese-catalyzed N-alkylation reaction of
amines with alcohols via hydrogen autotransfer strategy has been demonstrated.
The developed practical catalytic system including an inexpensive,
nontoxic, commercially available MnCl2 or MnBr(CO)5 as the metal salt and triphenylphosphine as a ligand provides
access to diverse aromatic, heteroaromatic, and aliphatic secondary
amines in moderate-to-high yields. In addition, this operationally
simple protocol is scalable to the gram level and suitable for synthesizing
heterocycles such as indole and resveratrol-derived amines known to
be active for Alzheimer’s disease.
A direct and convenient method for the C−H arylation and alkylation of electron-deficient N-heteroarenes with readily available organozinc reagents has been developed. This transformation could be readily performed in the absence of a transition-metal catalyst and external oxidants, affording a wide range of substituted heteroarenes with good functional group tolerance in good to excellent yields. The developed simple protocol is scalable to the gram level and suitable for late-stage modification of bioactive molecules and drugs.
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