Sulfonylimino Group Transfer Reaction Using Imino-λ3-iodanes with I2 as Catalyst Under Metal-free Conditions

被引：10

作者：

Yoshimura, Akira ^{[1
,2
]}

Makitalo, Cody L. ^{[2
]}

Jarvi, Melissa E. ^{[2
]}

Shea, Michael T. ^{[2
]}

Postnikov, Pavel S. ^{[1
]}

Rohde, Gregory T. ^{[3
]}

Zhdankin, Viktor V. ^{[2
]}

Saito, Akio ^{[4
]}

Yusubov, Mekhman S. ^{[1
]}

机构：

[1] Tomsk Polytech Univ, Res Sch Chem & Appl Biomed Sci, Tomsk 634050, Russia

[2] Univ Minnesota, Dept Chem & Biochem, Duluth, MN 55812 USA

[3] Marshall Sch, Duluth, MN 55811 USA

[4] Tokyo Univ Agr & Technol, Inst Engn, Div Appl Chem, 2-24-16 Naka Cho, Koganei, Tokyo 1848588, Japan

来源：

MOLECULES | 2019年 / 24卷 / 05期

基金：

俄罗斯科学基金会;

关键词：

iminoiodanes; imination; sulfide; sulfilimine; phosphine; iminophosphorane; amidyl radical; catalytic cycle; iodine; N-SULFONYLSULFILIMINES; CYCLIZATION REACTIONS; HYPERVALENT IODINE; NITRENE TRANSFER; SULFIDES; AZIRIDINATION; SULFIMIDATION; SULFILIMINES; SULFOXIMINES; IMINATION;

D O I：

10.3390/molecules24050979

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A new practical procedure of imination for sulfide has been developed. The treatment of (N-tosylimino)-phenyl-lambda(3)-iodane, PhINTs, with various sulfides in the presence of a catalytic amount of I-2 under metal-free conditions affords the corresponding N-tosylsulfilimine compounds with moderate to good yields. This facile transfer procedure of the sulfonylimino group can also be applied to triphenylphosphine to produce the respective iminotriphenylphosphoranes in high yields. According to the reaction mechanism studies, the process of imination from (N-tosylimino)-phenyl-lambda(3)-iodane to sulfide under the conditions may involve radical steps within the reaction mechanism.

引用

页数：11

共 56 条

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