Reversal Reactivity of β-Alkylnitroalkenes as 1,3-Binucleophiles: Application to Nitroarenes using Organocatalysis

An efficient pyrrolidine:4-ClBzOH salt (catalyst IV) catalyzed [3+3] cyclization reaction of beta-alkyl-substituted nitroalkenes as 1,3-binucleophiles with various beta-aryl/alkyl/alkenyl-substituted acroleins in an open-atmosphere is reported. Eventually, this tunable organocatalytic reaction creates one C-C and C=C bonds selectively that turns out to have a wide substrate scope, which affords a series of substituted nitroarenes in good to high yields. In addition, several other positive features are associated with this organocatalytic approach such as evading toxic metal-catalysts, no need for external oxidant and nitrating agent, 100% carbon-economical, excellent tolerance of functionalities, water as a sole by-product, circumventing of pre-functionalized arenes etc. Moreover, a range of important hetero-and carbocycles such as 2-arylcarbazole, 2,6-diphenylindole, 2'-chloro-1,1':4',1 ''-terphenyl and 1:1':4',1 ''-terphenyl were accessed from nitroarenes through our unique methods.

Automated summary

The organic catalytic reaction efficiently produces a range of substituted nitroarenes with high yields and wide substrate scope, while avoiding the use of toxic metal catalysts.