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Reversal Reactivity of β‐Alkylnitroalkenes as 1,3‐Binucleophiles: Application to Nitroarenes using Organocatalysis
Author(s) -
Majee Debashis,
Goud S Banuprakash,
Guin Soumitra,
Rathor Shikha S.,
Patel Ashvani K.,
Samanta Sampak
Publication year - 2021
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202100216
Subject(s) - chemistry , organocatalysis , reactivity (psychology) , catalysis , pyrrolidine , terphenyl , aryl , substrate (aquarium) , salt (chemistry) , alkyl , combinatorial chemistry , organic chemistry , enantioselective synthesis , medicine , alternative medicine , oceanography , pathology , geology
Abstract An efficient pyrrolidine : 4‐ClBzOH salt (catalyst IV ) catalyzed [3+3] cyclization reaction of β‐alkyl‐substituted nitroalkenes as 1,3‐binucleophiles with various β‐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.