Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 140, Issue 29, Pages 9074-9077Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b05245
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Funding
- Eli Lilly and Company through the Lilly Research Award Program (LRAP)
- DOE [DE-FG02-05ER15690]
- NIH [1S10 OD020022]
- NSF [CHE-1048642]
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A Cu-catalyzed method has been identified for aerobic oxidative dimerization of carbazoles and diarylamines to the corresponding N-N coupled bicarbazoles and tetraarylhydrazines. The reactions proceed under mild conditions (1 atm O-2, 60-80 degrees C) with a catalyst composed of CuBr.dimethylsulfide and N,N-dimethylaminopyridine. Reactions between carbazole and diarylamines show unusually selective cross-coupling, even with a 1:1 ratio of the two substrates. This behavior was found to arise from reversible formation of the tetraarylhydrazine. Formation of this species is kinetically favored, but cleavage of the N-N bond under the reaction conditions leads to selective formation of the thermodynamically favored cross-coupling product.
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