کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1360608 981442 2009 9 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Coulombic effects on the traceless Staudinger ligation in water
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Coulombic effects on the traceless Staudinger ligation in water
چکیده انگلیسی

The traceless Staudinger ligation can be mediated by phosphinothiols under physiological conditions. Proximal positive charges are necessary to achieve that transformation, presumably because those charges discourage protonation of the key iminophosphorane intermediate. Here, a series of cationic phosphinothiols is used to probe Coulombic effects on the traceless Staudinger ligation in aqueous buffers. The reagent bis(m-N,N-dimethylaminomethylphenyl)phosphinomethanethiol (3) is found to be superior to others, both in its ability to mediate the traceless Staudinger ligation in water and in the efficiency of its synthesis.

Consideration of Coulombic interactions enables phosphinothiols to mediate a traceless Staudinger ligation efficiently in water.Figure optionsDownload as PowerPoint slide

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Bioorganic & Medicinal Chemistry - Volume 17, Issue 3, 1 February 2009, Pages 1055–1063
نویسندگان
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