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Iridium-Catalyzed Alkylation of Amine and Nitrobenzene with Alcohol to Tertiary Amine under Base- and Solvent-Free Conditions

Author:
Li, Chao, Wan, Ke-feng, Guo, Fu-ya, Wu, Qian-hui, Yuan, Mao-lin, Li, Rui-xiang, Fu, Hai-yan, Zheng, Xue-li, Chen, Hua
Source:
Journal of organic chemistry 2019 v.84 no.4 pp. 2158-2168
ISSN:
1520-6904
Subject:
alkylation, chemical structure, hydrogen, nitrobenzenes, organic chemistry, primary amines, solvents, tertiary amines
Abstract:
Herein, an efficient and green method for the selective synthesis of tertiary amines has been developed that involves iridium-catalyzed alkylation of various primary amines with aromatic or aliphatic alcohols. Notably, the catalytic protocol enables this transformation in the absence of additional base and solvent. Furthermore, the alkylation of nitrobenzene with primary alcohol to tertiary amine has also been achieved by the same catalytic system. Deuterium-labeling experiments and a series of control experiments were conducted, and the results suggested that an intermolecular borrowing hydrogen pathway might exist in the alkylation process.
Agid:
6310438