Copper-Catalyzed Oxidative C(sp3)–H Functionalization for Facile Synthesis of 1,2,4-Triazoles and 1,3,5-Triazines from Amidines
- 29 May 2015
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 17 (12), 2894-2897
- https://doi.org/10.1021/acs.orglett.5b00995
Abstract
A facile and versatile catalytic system involving copper catalyst, K3PO4 as the base, and O2 as the oxidant has been developed to enable efficient synthesis of 2,4,6-trisubstituted and 2,6-disubstituted 1,3,5-triazines and 1,3-disubstituted 1,2,4-triazoles from amidines with trialkylamines, DMSO, and DMF as the reaction partners, respectively. This protocol features inexpensive metal catalyst, green oxidant, good functional group tolerance, and high regioselectivity, providing an efficient entry to those products that are challenging to prepare by traditional methods. A single-electron-transfer (SET) mechanism is proposed for these transformations.Keywords
Funding Information
- Ministry of Science and Technology of the People's Republic of China (2011CB808600)
- China Postdoctoral Science Foundation (2014M562165)
- National Natural Science Foundation of China (21172076, 21420102003)
- Natural Science Foundation of Jiangxi Province (20141BBG70070, 20151BAB203011)
- Natural Science Foundation of Guangdong Province (10351064101000000)
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