Synthesis and Structure of Hypervalent Iodine(III) Reagents Containing Phthalimidate and Application to Oxidative Amination Reactions

被引：64

作者：

Kiyokawa, Kensuke ^{[1
]}

Kosaka, Tomoki ^{[1
]}

Kojima, Takumi ^{[1
]}

Minakata, Satoshi ^{[1
]}

机构：

[1] Osaka Univ, Dept Appl Chem, Grad Sch Engn, Suita, Osaka 5650871, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 46期

关键词：

amination; amines; hypervalent iodine reagents; phthalimides; rearrangement; C-H BONDS; BETA-KETO-ESTERS; CATALYZED REARRANGEMENT; STABLE AZIDOIODINANES; TERTIARY-AMINES; AZIDATION; DIAMINATION; CHEMISTRY; AZIRIDINATIONS; ADJACENT;

D O I：

10.1002/anie.201506805

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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 insitu from secondary amines and aldehydes.

引用

页码：13719 / 13723

页数：5

共 59 条

[1]

Akai S, 1996, HETEROCYCLES, V42, P47

[2] The Productive Merger of Iodonium Salts and Organocatalysis: A Non-photolytic Approach to the Enantioselective α-Trifluoromethylation of Aldehydes [J].