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C3‐Alkenylation between Pyrroles and Aldehydes Mediated by a Brønsted Acid and a Brønsted Base
Author(s) -
Sahu Samrat,
Roy Avijit,
Gorai Mahadeb,
Guria Sudip,
Sudan Maji Modhu
Publication year - 2019
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.201901228
Subject(s) - chemistry , brønsted–lowry acid–base theory , base (topology) , selectivity , combinatorial chemistry , redox , catalysis , transition metal , organocatalysis , organic chemistry , enantioselective synthesis , mathematical analysis , mathematics
A transition‐metal‐free, redox‐neutral, organocatalytic C3‐alkenylation of pyrroles is reported. Readily available aldehydes were employed as alkenylating agent and the reaction tolerates several key functional groups. The E ‐alkenylated products were isolated in moderate to exclusive selectivity. A one‐pot two‐fold alkenylation strategy is also developed for further downstream modifications. To show the applicability, synthetically challenging indolylpyrrole derivatives were synthesized using Cadogan cyclization.