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Manganese‐Catalysed C−H Activation: A Regioselective C−H Alkenylation of Indoles and other (hetero)aromatics with 4‐Hydroxy‐2‐Alkynoates Leading to Concomitant Lactonization
Author(s) -
Kumar Anil,
Muniraj Nachimuthu,
Prabhu Kandikere Ramaiah
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900678
Subject(s) - regioselectivity , chemistry , manganese , steric effects , catalysis , indole test , substrate (aquarium) , functional group , stereochemistry , medicinal chemistry , organic chemistry , oceanography , polymer , geology
A manganese‐catalyzed C−H bond alkenylation of indoles at C2‐position with 4‐hydroxy‐2‐alkynoates leading to concomitant lactonization under removable directing group strategy has been disclosed. This lactonization strategy exhibits regioselectivity, a broad substrate scope, and a good functional group tolerance furnishing the products in low to high yields. The regioselectivity is guided by the electronic effect of the ester group as well as the steric bulk at the C4‐position of the 4‐hydroxy‐2‐alkynoates. After the reaction, the directing group has been readily removed to obtain N−H free indole.