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Iron‐Catalyzed Tandem C‐N and C–C bond Cleavage in Diaryl Methanamines: Use of Electron‐Rich Arenes as Leaving Group to Generate Triaryl Methanes
Author(s) -
Paul Dipankar,
Khatua Snehadrinarayan,
Chatterjee Paresh N.
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201802245
Subject(s) - chemistry , cleavage (geology) , tandem , bond cleavage , steric effects , catalysis , nucleophile , medicinal chemistry , organic synthesis , photochemistry , stereochemistry , organic chemistry , geotechnical engineering , engineering , materials science , fracture (geology) , composite material
A facile FeCl 3 catalyzed tandem C−N and C−C bond cleavage in N ‐protected diaryl methanamines has been studied where the C−C bond cleavage, interestingly, results in the release of electron‐rich and sterically bulky arenes such as 1,3,5‐trimethoxybenzene or 3,5‐dimethoxytoluene. The tandem bond cleavage reaction generates triaryl methanes in mild conditions under air atmosphere. We found success in isolating the intermediate, formed through the preliminary C−N bond cleavage, and then converted the isolated intermediate to the final triaryl methanes by affecting the subsequent C−C bond cleavage. Several nucleophiles such as indoles, furans, 4‐methoxythiophenol and 1,3‐dimethoxybenzene were found effective under Lewis acidic conditions to cause the unusual yet facile tandem bond cleavage reaction in the diaryl methanamines. Use of electron‐rich and sterically bulky arenes as leaving groups in the present work highlights an innovative concept, which may potentially open up parallel avenues in organic synthesis.