In situ Generated Ruthenium Catalyst Systems Bearing Diverse N-Heterocyclic Carbene Precursors for Atom-Economic Amide Synthesis from Alcohols and Amines

In situ Generated Ruthenium Catalyst Systems Bearing Diverse N-Heterocyclic Carbene Precursors for Atom-Economic Amide Synthesis from Alcohols and Amines

Bibliographic Details
Parent link:Chemistry - An Asian Journal
Vol. 13, iss. 4.— 2018.— [С. 440–448]
Corporate Author: Национальный исследовательский Томский политехнический университет (ТПУ) Институт природных ресурсов (ИПР) Кафедра технологии органических веществ и полимерных материалов (ТОВПМ)
Other Authors: Cheng Hua, Mao-Qian Xiong, Chuan-Xiang Cheng, Hua-Jing Wang, Qiang Lu, Hong-Fu Liu, Fu-Bin Yao, Cheng Chen, Verpoort F. V. K. Frensis Valter Kornelius
Summary:Title screen
The transition-metal-catalyzed direct synthesis of amides from alcohols and amines is herein demonstrated as a highly environmentally benign and atom-economic process. Among various catalyst systems, in situ generated N-heterocyclic carbene (NHC)-based ruthenium (Ru) halide catalyst systems have been proven to be active for this transformation. However, these existing catalyst systems usually require an additional ligand to achieve satisfactory results. In this work, through extensive screening of a diverse variety of NHC precursors, we discovered an active in situ catalyst system for efficient amide synthesis without any additional ligand. Notably, this catalyst system was found to be insensitive to the electronic effects of the substrates, and various electron-deficient substrates, which were not highly reactive with our previous catalyst systems, could be employed to afford the corresponding amides efficiently. Furthermore, mechanistic investigations were performed to provide a rationale for the high activity of the optimized catalyst system. NMR-scale reactions indicated that the rapid formation of a Ru hydride intermediate (signal at delta=−7.8 ppm in the 1H NMR spectrum) after the addition of the alcohol substrate should be pivotal in establishing the high catalyst activity. Besides, HRMS analysis provided possible structures of the in situ generated catalyst system.
Language:English
Published: 2018
Subjects:
электронный ресурс
труды учёных ТПУ
каталитические системы
синтез
амиды
переходные металлы
спирты
амины
лиганды
Online Access:https://doi.org/10.1002/asia.201701734
Format: Electronic Book Chapter
KOHA link:https://koha.lib.tpu.ru/cgi-bin/koha/opac-detail.pl?biblionumber=667264

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