A Highly Chemoselective and Practical Alkynylation of Thiols
A Highly Chemoselective and Practical Alkynylation of Thiols
复制标题
DOI：
10.1021/ja4044196
复制
发表时间：
2013-07-03
影响因子：
15
通讯作者：
Waser, Jerome
中科院分区：
文献类型：
--
作者：
Frei, Reto;Waser, Jerome
已经开发出利用高价碘炔转移试剂 TIPS-乙炔基-苯并氧酮的硫醇-炔基化方法。这种可扩展的反应在室温下使用市售试剂在敞口烧瓶中进行五分钟。该反应的范围很广，各种酚类、苄类、杂环类和脂肪族硫醇都可以进行炔基化，产率很高。该方法具有高度化学选择性，因为可以耐受大量的官能团。通过在含半胱氨酸的肽上轻松安装荧光团标签，已经证明了硫醇-炔基化在合成后精加工中的实用性。
A thiol-alkynylation procedure utilizing the hypervalent iodine alkyne transfer reagent TIPS-ethynyl-benziodoxolone has been developed. This scalable reaction proceeds in five minutes at room temperature in an open flask using commercially available reagents. The scope of the reaction is broad, with a variety of phenolic, benzylic, heterocyclic, and aliphatic thiols undergoing alkynylation in excellent yield. The method is highly chemoselective as a vast array of functional groups are tolerated. The utility of the thiol-alkynylation in postsynthetic elaboration has been demonstrated through the facile installment of a fluorophore tag on a cysteine-containing peptide.