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Ketene 3‐Component Staudinger Reaction (K‐3CSR) to β‐Lactams: A New Entry in the Class of Photoinduced Multicomponent Reactions
Author(s) -
Minuto Federica,
Lambruschini Chiara,
Basso Andrea
Publication year - 2021
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.202100577
Subject(s) - chemistry , ketene , imine , staudinger reaction , component (thermodynamics) , combinatorial chemistry , photochemistry , computational chemistry , organic chemistry , catalysis , physics , thermodynamics
The Staudinger synthesis of β‐lactams from imines and ketenes has been conducted photochemically only in very limited cases. Recent advances in the visible light mediated Wolff rearrangement of diazoketones allowed us to perform, for the first time, a 3‐component Staudinger reaction, by mixing aldehydes, amines and diazoketones in the dark and switching the light on after imine formation. The new photoinduced reaction parallels the classic methods in terms of efficiency/selectivity and adds to the existing multicomponent approaches for the preparation of combinatorial libraries of compounds. A thorough optimization of the reaction conditions was performed both for the classic two component reaction and for the novel three component version of the photoinduced Staudinger reaction.