Premium
Transition‐Metal‐Free Tunable Chemoselective N Functionalization of Indoles with Ynamides
Author(s) -
Hentz Alexandre,
Retailleau Pascal,
Gandon Vincent,
Cariou Kevin,
Dodd Robert H.
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201402767
Subject(s) - surface modification , nitrogen atom , chemistry , scope (computer science) , combinatorial chemistry , transition metal , nitrogen , metal , atom (system on chip) , computational chemistry , organic chemistry , group (periodic table) , catalysis , computer science , programming language , embedded system
Two unprecedented N functionalizations of indoles with ynamides are described. By varying the electron‐withdrawing group on the ynamide nitrogen atom, either Z ‐indolo‐etheneamides or indolo‐amidines can be selectively obtained under the same metal‐free reaction conditions. The scope and synthetic potential of these reactions, as well as some mechanistic insights provided by DFT calculations, are reported.