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Tungsten-Catalyzed Direct N-Alkylation of Amines with Alcohols
preprintsubmitted on 29.07.2020, 08:18 and posted on 30.07.2020, 06:48 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.