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SF-炔烃的区域和立体选择性加氢元素反应及进一步官能化

Regio- and Stereoselective Hydroelementation of SF -Alkynes and Further Functionalizations.

作者信息

Popek Lucas, Cabrera-Trujillo Jorge Juan, Debrauwer Vincent, Blanchard Nicolas, Miqueu Karinne, Bizet Vincent

机构信息

Université de Haute-Alsace, Université de Strasbourg, CNRS, LIMA, UMR 7042, 68000, Mulhouse, France.

CNRS/Université de Pau et des Pays de l'Adour, E2S-UPPA, IPREM UMR 5254, 64053, Pau cedex 09, France.

出版信息

Angew Chem Int Ed Engl. 2023 May 2;62(19):e202300685. doi: 10.1002/anie.202300685. Epub 2023 Mar 30.

Abstract

Herein is described a fully regio- and stereoselective hydroelementation reaction of SF -alkynes with N, O and S-nucleophiles and further functionalization of the corresponding Z-(hetero)vinyl-SF intermediates, a suitable platform to access α-SF ketones and esters, β-SF amines and alcohols under mild reaction conditions. Experimental and computational comparative studies between SF - and CF -alkynes have been performed to highlight and explain the difference of reactivity and selectivity observed between these two fluorinated motifs.

摘要

本文描述了SF-炔烃与N、O和S亲核试剂的完全区域和立体选择性加氢元素化反应,以及相应的Z-(杂)乙烯基-SF中间体的进一步官能化,这是一个在温和反应条件下获得α-SF酮和酯、β-SF胺和醇的合适平台。已经对SF-炔烃和CF-炔烃进行了实验和计算比较研究,以突出和解释在这两个氟化基团之间观察到的反应性和选择性差异。

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