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A Tunable Trifluoromethyliodonium Reagent
Author(s) -
Liebing Phil,
Kalim Jorna,
Arefyeva Natalia,
Oehler Florian,
Wickleder Mathias,
Togni Antonio
Publication year - 2019
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.201903623
Subject(s) - hypervalent molecule , reagent , trifluoromethyl , chemistry , trifluoromethylation , reactivity (psychology) , medicinal chemistry , bond cleavage , organic chemistry , catalysis , alkyl , medicine , alternative medicine , pathology
Four complexes of MCl 4 (M=Ti, Zr, Hf) with the hypervalent trifluoromethyl iodine reagent trifluoromethyl‐1,3‐dihydro‐3,3‐dimethyl‐1,2‐benziodoxole ( 1 ,=L) are described. With TiCl 4 , an I−O bond cleavage occurs, leading to the formation of the trifluoromethyliodonium alcoholate complexes [Ti 2 Cl 6 (L) 4 ]Cl 2 ( 2 a ) and Ti 2 Cl 8 (L) ( 2 b ). Reactions with ZrCl 4 and HfCl 4 form the complexes ZrCl 4 (L) 2 ( 3 ) and HfCl 4 (L) 2 ( 4 ), respectively, wherein the original I−O bond is retained and elongated compared to that in free 1 . Therefore, the reactivity of 1 can be easily and practically fine‐tuned by addition of different metal chlorides, following the order ZrCl 4 /HfCl 4
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