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Visible Light‐Induced, Metal‐Free Denitrative [3+2] Cycloaddition for Trisubstituted Pyrrole Synthesis
Author(s) -
Karki Bhupal S.,
Devi Lalita,
Pokhriyal Ayushi,
Kant Ruchir,
Rastogi Namrata
Publication year - 2019
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201901068
Subject(s) - regioselectivity , cycloaddition , chemistry , pyrrole , visible spectrum , nitro , photochemistry , functional group , reaction conditions , catalysis , combinatorial chemistry , organic chemistry , materials science , alkyl , polymer , optoelectronics
A metal‐free, regioselective synthesis of trisubstituted pyrroles has been developed through a formal [3+2] cycloaddition reaction between 2H‐azirines and nitroalkenes under visible light/photoredox‐catalyzed conditions. The reaction proceeds through 2H‐azaallenyl radical addition on β‐nitrostyrenes in a Michael fashion followed by a base‐mediated denitration reaction. The directive group influence of the nitro group controls the regiochemistry of the reaction.