Synthesis of 5-Iodo-1,2,3-triazoles from Organic Azides and Terminal Alkynes: Ligand Acceleration Effect, Substrate Scope, and Mechanistic Insights

被引：38

作者：

Barsoum, David N. ^{[1
]}

Brassard, Christopher J. ^{[1
]}

Deeb, Jason H. A. ^{[1
]}

Okashah, Najeah ^{[1
]}

Sreenath, Kesavapillai ^{[1
]}

Simmons, J. Tyler ^{[1
]}

Zhu, Lei ^{[1
]}

机构：

[1] Florida State Univ, Dept Chem & Biochem, Tallahassee, FL 32306 USA

来源：

SYNTHESIS-STUTTGART | 2013年 / 45卷 / 17期

基金：

美国国家科学基金会;

关键词：

azides; alkynes; copper; catalysis; heterocycles; cyclizations; triazoles; halogenation; iodine; ONE-POT SYNTHESIS; CYCLOADDITION REACTION; 1,2,3-TRIAZOLES; 1-IODOALKYNES; PALLADIUM; CATALYST;

D O I：

10.1055/s-0033-1339312

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An improved method has been developed for the preparation of 5-iodo-1,2,3-triazoles directly from organic azides and terminal alkynes by a reaction mediated by copper(I) and iodinating agents generated in situ. The major methodological advance of the current procedure is that it provides a high conversion and good iodo/proto selectivity with a broad range of substrates without using an excess of the alkyne, which was required in the previous method. The use of an accelerating ligand is essential to the success of reactions involving unreactive azides or alkynes. New mechanistic insights are provided, including the confirmation that a 1-iodoalkyne is formed as a key intermediate under the established conditions for the reaction.

引用

页码：2372 / 2386

页数：15

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