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Nucleophilic Iron Complexes in Proton‐Transfer Catalysis: An Iron‐Catalyzed Dimroth Cyclocondensation
Author(s) -
Baykal Aslihan,
Zhang Dihan,
Knelles Jakob,
Alt Isabel T.,
Plietker Bernd
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.201900821
Subject(s) - indoline , chemistry , nitrene , catalysis , amination , nucleophile , combinatorial chemistry , medicinal chemistry , organic chemistry , photochemistry
The nucleophilic iron complex Bu 4 N[Fe(CO) 3 (NO)] (TBA[Fe]) is an active catalyst in C−H‐amination but also in proton‐transfer catalysis. Herein, we describe the successful use of this complex as a proton‐transfer catalyst in the cyclocondensation reaction between azides and ketones to the corresponding 1,2,3‐triazoles. Cross‐experiments indicate that the proton‐transfer catalysis is significantly faster than the nitrene‐transfer catalysis, which would lead to the C−H amination product. An example of a successful sequential Dimroth triazole–indoline synthesis to the corresponding triazole‐substituted indolines is presented.