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Chiral Ferrocenyl−Iodotriazoles and −Iodotriazoliums as Halogen Bond Donors. Synthesis, Solid State Analysis and Catalytic Properties.
Author(s) -
Aubert Emmanuel,
Doudouh Abdelatif,
Wenger Emmanuel,
Sechi Barbara,
Peluso Paola,
Pale Patrick,
Mamane Victor
Publication year - 2022
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.202100927
Subject(s) - chemistry , trifluoromethanesulfonate , catalysis , combinatorial chemistry , halogen bond , halogen , enantioselective synthesis , context (archaeology) , organic chemistry , alkyl , paleontology , biology
Despite the increasing number of applications based on halogen bond (XB), asymmetric catalysis purely based on such supramolecular interactions still remains a huge challenge. The first step toward its development is the design of appropriate XB chiral donor molecules with good catalytic properties. In this context, we report the synthesis of a series of iodinated compounds based on the triazole or triazolium ring and possessing the planar chirality of ferrocene. Their XB donor property was attested by X‐ray diffraction analysis, showing short I⋅⋅⋅N and I⋅⋅⋅F interactions in the triazole‐based derivatives and in the tetrafluoroborate salt of a idodotriazolium, respectively. The potential of these compounds to act as XB‐based catalysts was demonstrated in the aza‐Diels‐Alder reaction involving an imine and a diene. Whereas triazole‐based derivatives were inactive in this reaction, the triflate salts of iodotriazoliums delivered the expected cycloadduct with high yield.