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磺酰叠氮化合物中 S-N 键的区域选择性断裂:磺酰供体。

Regiospecific Cleavage of S-N Bonds in Sulfonyl Azides: Sulfonyl Donors.

机构信息

Henan Key Laboratory of Organic Functional Molecule and Drug Innovation, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering , Henan Normal University , Xinxiang , Henan 453007 , China.

出版信息

J Org Chem. 2019 Apr 5;84(7):3919-3926. doi: 10.1021/acs.joc.8b03046. Epub 2019 Mar 19.

DOI:10.1021/acs.joc.8b03046
PMID:30854857
Abstract

Sulfonyl azides have been widely used as sulfonamido, diazo, and azido donors, as well as all-nitrogen 1,3-dipoles donors in synthetic chemistry. Here, the sulfonyl azides were used as efficient sulfonyl donors, which is very unusual. Trifluoromethanesulfonic acid-induced formation of the sulfonyl cation reactive species from sulfonyl azides was developed and used for the first time to couple various inactivated arenes to prepare sulfones at ambient temperature.

摘要

磺酰叠氮化物在合成化学中被广泛用作磺酰胺基、重氮基和叠氮基供体,以及全氮 1,3-二极体供体。在这里,磺酰叠氮化物被用作有效的磺酰供体,这是非常不寻常的。发展了三氟甲磺酸诱导磺酰叠氮化物形成磺酰阳离子反应性物种,并首次将其用于在环境温度下偶联各种失活芳基以制备砜。

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