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Cooperative Effects in Switchable Catalysis: Enhancing Double‐Click Reaction Yield of Symmetrical Rotaxanes
Author(s) -
Ghosh Amit,
Paul Indrajit,
Schmittel Michael
Publication year - 2021
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.202108269
Subject(s) - click chemistry , homoleptic , cycloaddition , yield (engineering) , catalysis , chemistry , combinatorial chemistry , materials science , organic chemistry , metal , metallurgy
Reversible switching between the closed cyclic dimeric assembly [Cu 2 ( 1 ) 2 ] 2+ (OFF state) and the extended dimeric homoleptic complex [FeCu 2 ( 1 ) 2 ] 4+ (ON State) by addition/removal of Fe 2+ triggered catalysis of a double‐click reaction and high yield preparation of [2]rotaxanes. Mechanistic and computational studies provide valuable general insight for double‐click strategies by revealing cooperative effects in the second cycloaddition step due to a distance‐tolerant preorganization of the first‐click product by the two copper(I)‐loaded phenanthroline subunits of [FeCu 2 ( 1 ) 2 ] 4+ .