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Scope and Limitations of TBA[Fe]‐Catalyzed Carbene Transfer to X−H‐bonds – Indication of a Mechanistic Dichotomy
Author(s) -
Röske Annika,
Alt Isabel,
Plietker Bernd
Publication year - 2019
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201900459
Subject(s) - carbene , silanes , chemistry , nucleophile , catalysis , medicinal chemistry , photochemistry , organic chemistry , silane
Abstract An in‐depth study of carbene transfer reactions into polar X−H‐bonds catalyzed by the nucleophilic Fe‐complex Bu 4 N[Fe(CO) 3 (NO)] (TBA[Fe]) is presented. Whereas alcohols are unreactive, thiols and secondary amines are reactive, silanes showed modest activities. Hammett correlations indicate the presence of an X−H‐acidity dependent mechanistic dichotomy.