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Silver‐Induced C α (sp 3 )–H Activation of Benzylamines Followed by [1,5]‐ versus [1,3]‐Rearrangement: A Strategy towards the Regioselective Synthesis of Spiro‐Dihydropyrroles
Author(s) -
Mondal Animesh,
Mukhopadhyay Chhanda
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701103
Subject(s) - chemistry , regioselectivity , isatin , benzylamine , medicinal chemistry , bond cleavage , cleavage (geology) , silver acetate , pyrrole , organic chemistry , catalysis , geotechnical engineering , fracture (geology) , engineering
For the first time in pyrrole chemistry, silver‐mediated C α (sp 3 )–H bond activation of benzylamines followed by [1,5]‐ versus [1,3]‐rearrangement towards the regioselective synthesis of spiro‐dihydropyrrole derivatives has been achieved. The reaction proceeds through cleavage of the benzylamine C–N bond promoted by the crucial silver carbonate followed by a regioselective [1,5]‐rearrangement with dialkyl but‐2‐ynedioate in the presence of isatin or N ‐methylisatin. Equally, N ‐substituted isatin with benzyl, allyl, ethyl, propyl, and n ‐butyl substituents proceeds through an alternate [1,3]‐rearrangement strategy. The study highlights the recycling of silver species and for selective use in oxidative C–N and C–C coupling reactions.