title: Synthesis and Structure of Hypervalent Iodine(III) Reagents Containing Phthalimidate and Application to Oxidative Amination Reactions.
abstract: 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.
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871 (Japan). kiyokawa@chem.eng.osaka-u.ac.jp.
authors.forename: Kensuke
authors.initials: K
authors.lastname: Kiyokawa
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871 (Japan).
authors.forename: Tomoki
authors.initials: T
authors.lastname: Kosaka
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871 (Japan).
authors.forename: Takumi
authors.initials: T
authors.lastname: Kojima
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871 (Japan). minakata@chem.eng.osaka-u.ac.jp.
authors.forename: Satoshi
authors.initials: S
authors.lastname: Minakata
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry; D000586:Amination; D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D007455:Iodine / Q000737:chemistry*; D007462:Iodobenzenes; D007463:Iodobenzoates / Q000138:chemical synthesis / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010797:Phthalimides / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D000588:Amines; D007462:Iodobenzenes; D007463:Iodobenzoates; D010797:Phthalimides; C476101:o-iodoxybenzoic acid; D007455:Iodine
keywords: amination; amines; hypervalent iodine reagents; phthalimides; rearrangement