期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 138, 期 38, 页码 12605-12614出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b07486
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资金
- Institute for Basic Science in Korea [IBS-R010-D1]
- Ministry of Science, ICT & Future Planning, Republic of Korea [IBS-R010-D1-2016-A00] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
- National Research Foundation of Korea [21A20151513223] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
Primary arylamines are an important unit broadly found in synthetic, biological, and materials science. Herein we describe the development of a (NHC)Cu system that mediates a direct C-H amidation of (hetero)arenes by using N-chlorocarbamates or their sodio derivatives as the practical amino sources. A fade stoichiometric reaction of reactive copper-aryl intermediates with the amidating reagent led us to isolate key copper arylcarbamate species with the formation of a C-N bond. The use of (BuONa)-Bu-t base made this transformation catalytic under mild conditions. The present (NHC)Cu-catalyzed C-H amidation works efficiently and selectively on a large scale over a range of arenes including polyfluorobenzenes, azoles, and quinoline N-oxides. Deprotection of the newly installed carbamate groups such as Boc and Cbz was readily performed to afford the corresponding primary arylamines.
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