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Tungsten-Catalyzed Direct N-Alkylation of Amines with Alcohols

preprint
submitted on 29.07.2020 and posted on 30.07.2020 by Xiao-Bing Lan, Zongren Ye, Weikang Li, Jiahao Liu, Ming Huang, Yan Liu, Zhuofeng Ke
The implementation of earth-abundant metals mediated chemistry is a major goal in homogeneous catalysis. Borrowing hydrogen/hydrogen autotransfer (BH/HA) reaction, as a straightforward and sustainable synthetic method, has attracted considerable attention in the development of earth-abuandant metal catalysts. Herein, we report a tungsten-catalyzed N-alkylation reaction of amines with primary alcohols via BH/HA. This phosphine-free W(phen)(CO)4 (phen=1,10-phenthroline) system was demonstrated as a practical and easily accessible in-situ catalysis for a broad range of amines and alcohols (up to 49 examples, including 16 previously undisclosed products). Notably, this tungsten system can tolerate numerous functional groups, especially the challenging substrates with sterically hindered substituents, or heteroatoms. Mechanistic insights based on experimental and computational studies are also provided.

History

Email Address of Submitting Author

kezhf3@mail.sysu.edu.cn

Institution

Sun Yat-sen University

Country

China

ORCID For Submitting Author

0000-0001-9064-8051

Declaration of Conflict of Interest

no conflict of interest

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