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 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 o...

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Bibliographic Details
Published in:Asian journal of organic chemistry 2021-07, Vol.10 (7), p.1650-1654
Main Authors: Majee, Debashis, Goud, S Banuprakash, Guin, Soumitra, Rathor, Shikha S., Patel, Ashvani K., Samanta, Sampak
Format: Article
Language:English
Subjects:
Acrolein
Aromatic compounds
Catalysts
domino
Nitration
nitroarenes
Organic chemistry
organocatalysis
Oxidizing agents
Substitutes
Substrates
β-alkyl-nitroalkenes
β-substituted acroleins
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Summary: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. An efficient pyrrolidine/4‐ClBzOH salt‐catalyzed [3+3] cyclization of β‐alkyl‐substituted nitroalkenes and β‐aryl/alkyl/alkenyl‐substituted acroleins is reported. This oxidant‐metal‐free route delivers nitroarenes in satisfactory yields. Furthermore, few useful molecules such as 2‐phenylcarbazole, 2,6‐diphenylindole, 2′‐chloro‐1,1′ : 4′,1′′‐terphenyl, 1 : 1′ : 4′,1′′‐terphenyl etc could synthesize from nitroarenes by simple synthetic operations.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.202100216