Open AccessPalladium-Catalyzed α-Arylation of Aryl Nitromethanes
Author(s) -
Kelsey F. VanGelder,
Marisa C. Kozlowski
Publication year - 2015
Publication title -
organic letters
Language(s) - Uncategorized
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.5b02793
Subject(s) - nitromethane , chemistry , aryl , methylamines , catalysis , palladium , combinatorial chemistry , reactivity (psychology) , organic chemistry , medicine , alkyl , alternative medicine , pathology
Catalytic conditions for the α-arylation of aryl nitromethanes have been discovered using parallel microscale experimentation, despite two prior reports of the lack of reactivity of these aryl nitromethane precursors. The method efficiently provides a variety of substituted, isolable diaryl nitromethanes. In addition, it is possible to sequentially append two different aryl groups to nitromethane. Mild oxidation conditions were identified to afford the corresponding benzophenones via the Nef reaction, and reduction conditions were optimized to afford several diaryl methylamines.