4.4 Article

One-pot preparation of (RSe)2CF2 and (RS)2CF2 compounds via insertion of TMSCF3-derived difluorocarbene into diselenides and disulfides

Journal

TETRAHEDRON
Volume 75, Issue 31, Pages 4167-4173

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2019.04.042

Keywords

Difluorocarbene; TMSCF3; Insertion; Diselenides; Disulfides

Funding

  1. Loker Hydrocarbon Research Institute

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A method for the first direct insertion of difluorcarbene, generated from TMSCF3, into diselenides and disulfides is disclosed, producing novel difluoromethyl diselenoacetals and difluoromethyl dithioacetals. The reaction conditions tolerate a range of synthetically useful and biologically relevant functional groups. The process is scalable, with two representative compounds prepared at a gram-scale in good yields, and it utilizes cheap and available reagents. (C) 2019 Elsevier Ltd. All rights reserved.

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