The rhodium-catalyzed transannulation of N-perfluoroalkyl-1,2,3-triazoles with aromatic and aliphatic terminal alkynes under microwave heating conditions afforded N-perfluoroalkyl-3,4-disubstituted pyrroles (major products) and N-fluoroalkyl-2,4-disubstituted pyrroles (minor products). The observed selectivities in the case of the reactions with aliphatic alkynes were high.
Nitrobenzenes substituted with electron-acceptor groups such as halogen, nitro, trifluoromethyl, pentafluorosulfanyl, or cyano underwent oxidative nucleophilic substitution with lithium salts of arylamines to afford N-aryl-2-nitroanilines.
Nitroaromatics substituted with electron-acceptor or electron-donor groups undergo vicarious nucleophilic substitution with the lithium salt of dichloromethane to provide chloromethyl-substituted nitroaromatics in good to high yields. The methodology represents a new strategy for the synthesis of benzyl chlorides.
Oxidative nucleophilic aromatic substitution for hydrogen of nitroaromatics with potassium alkoxides derived from primary, secondary or tertiary alcohols in the presence of oxygen was achieved. Mechanistic investigations suggest the formation...
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