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Synthesis and Structure of Hypervalent Iodine(III) Reagents Containing Phthalimidate and Application to Oxidative Amination Reactions
Author(s) -
Kiyokawa Kensuke,
Kosaka Tomoki,
Kojima Takumi,
Minakata Satoshi
Publication year - 2015
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.201506805
Subject(s) - hypervalent molecule , iodine , amination , reagent , oxidative phosphorylation , chemistry , combinatorial chemistry , organic chemistry , catalysis , biochemistry
A new class of hypervalent iodine reagents containing phthalimidate was synthesized, and structurally characterized by X‐ray analysis. The benziodoxole‐based reagent displays satisfactory solubility in common organic solvents and is reasonably stable in solution as well as in the solid state. The reagent was used for the oxidative amination of the C(sp 3 )H bond of N,N‐dimethylanilines. In addition, the reagent was also applicable to oxidative amination with rearrangement of trialkylamines as well as enamines that were prepared in situ from secondary amines and aldehydes.