The N-Alkylation of Sulfonamides with Alcohols in Water Catalyzed by the Water-Soluble Iridium Complex {Cp*Ir[6,6′-(OH)2bpy]( H2O)}[OTf]2

被引：128

作者：

Qu, Panpan ^{[1
]}

Sun, Chunlou ^{[1
]}

Ma, Juan ^{[1
]}

Li, Feng ^{[1
]}

机构：

[1] Nanjing Univ Sci & Technol, Key Lab Soft Chem & Funct Mat, Minist Educ, Nanjing 210094, Jiangsu, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2014年 / 356卷 / 2-3期

基金：

中国国家自然科学基金;

关键词：

alcohols; N-alkylation; hydrogen autotransfer; iridium; sulfonamides; water-soluble catalyst; ASYMMETRIC TRANSFER HYDROGENATION; DEPENDENT TRANSFER HYDROGENATION; ASTERISK-IR COMPLEX; CP-ASTERISK; ORGANIC-SYNTHESIS; DEHYDROGENATIVE OXIDATION; SELECTIVE ALKYLATION; REDUCTIVE AMINATION; EFFICIENT CATALYSTS; BORROWING HYDROGEN;

D O I：

10.1002/adsc.201300711

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The water-soluble iridium complex {Cp*Ir[6,6-(OH)(2)bpy](H2O)}[OTf](2) (Cp*=(5)-pentamethylcyclopentadienyl, bpy=2,2-bipyridine) was found to be a general and highly efficient catalyst for the N-alkylation of the poor nucleophilic sulfonamides with alcohols as alkylating agents in water. The presence of OH units in the bpy ligand is crucially important for the catalytic activity of the iridium complex. Mechanistic investigations revealed that the catalytically active species is a ligand-metal bifunctional iridium complex bearing an N,N-chelated 2,2-bipyridinated ligand and an aqua ligand. Notably, the present catalytic system and the proposed mechanism provide a new horizon and scope for the development of hydrogen autotransfer (or hydrogen-borrowing) processes.

引用

页码：447 / 459

页数：13

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