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Beilstein Journal Of Organic Chemistry

Publication date: 2021-09-06
Volume: 17 Pages: 2315 - 2320
Publisher: Beilstein-Institut

Author:

Winant, Pieterjan
Dehaen, Wim

Keywords:

Science & Technology, Physical Sciences, Chemistry, Organic, Chemistry, benzoquinone, diazonium salts, Green Chemistry, Meerwein arylation, photoredox, C-H ARYLATION, ARYLBORONIC ACIDS, BODIPY DYES, BENZOQUINONE, QUINONES, FUNCTIONALIZATION, DIAZONIUM, G0F6619N#54971555, 0305 Organic Chemistry, Organic Chemistry, 3405 Organic chemistry

Abstract:

A metal-free protocol for the direct bis-arylation of 2,5-dichlorobenzoquinone with aryldiazonium salts is reported. The reactive salts are generated in situ and converted to radicals through irradiation with visible light. Reaction products precipitate from the solvent, eliminating the need for purification and thus providing a novel green method for the synthesis of versatile bis-electrophiles.