Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 17, Pages 11905-11914Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c01325
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Funding
- National Natural Science Foundation of China [22078370, 21776318, 22078369, 22003077]
- Basic Science Center Project for the National Natural Science Foundation of China [72088101]
- Basic Science Center Project for the National Natural Science Foundation of China (Theory and Application of Resource and Environment Management in the Digital Economy Era)
- Natural Science Foundation of Hunan Province [2018JJ3868, 2020JJ4682]
- Fundamental Research Funds for Central South University [2020zzts401]
- Central South University
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A new methyl source, TMEDA, was identified and used to develop a protocol for direct C-H methylation of N-heteroarenes. The method features mild reaction conditions and a wide substrate scope.
Aiming at the valuable methylation process, readily available and inexpensive N, N, N', N'- tetramethylethylenediamine (TMEDA) was first identified as a new methyl source in photoredox-catalyzed transformation in this work. By virtue of this simple methylating reagent, a facile and practical protocol for the direct C-H methylation of N-heteroarenes was developed, featuring mild reaction conditions, broad substrate scope, and scalability. Mechanistic studies disclosed that a sequential photoredox, base-assisted proton shift, fragmentation, and tautomerization process was essentially involved.
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