Controlled thioamide vs. amide formation in the thioacid-azide reaction under acidic aqueous conditions

被引：15

作者：

Muehlberg, Michaela ^{[1
,2
]}

Siebertz, Kristina D. ^{[2
,3
]}

Schlegel, Brigitte ^{[2
]}

Schmieder, Peter ^{[2
]}

Hackenberger, Christian P. R. ^{[2
,3
]}

机构：

[1] Free Univ Berlin, Inst Chem & Biochem, D-14195 Berlin, Germany

[2] Forschungsinst Mol Pharmakol, D-13125 Berlin, Germany

[3] Humboldt Univ, Inst Organ & Bioorgan Chem, Inst Chem, D-12489 Berlin, Germany

来源：

CHEMICAL COMMUNICATIONS | 2014年 / 50卷 / 35期

关键词：

STAUDINGER LIGATION; SULFONYL AZIDES; BOND FORMATION; PEPTIDE; STRATEGIES; MECHANISM; ACETYLATION; PROTEINS;

D O I：

10.1039/c4cc00774c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The thioacid-azide reaction and its chemoselectivity were probed with alkyl azides for a potential application to form amide bonds in aqueous solvents. Our results reveal that under acidic conditions thioamides were formed as major reaction products suggesting a competing mechanism, whereas reactions forming amides predominated at slightly higher pH values.

引用

页码：4603 / 4606

页数：4

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