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A Photoredox Nozaki‐Hiyama Reaction Catalytic in Chromium

F. Calogero, Simone Potenti, Giandomenico Magagnano, Giampaolo Mosca, Andrea Gualandi, Marianna Marchini, Paola Ceroni, Pier Giorgio Cozzi

2022European Journal of Organic Chemistry16 citationsDOIOpen Access PDF

Abstract

Abstract Organochromium(III) species are multipurpose nucleophiles used in the synthesis of complex organic molecules due to their high functional group tolerance and extraordinary chemoselectivity for aldehydes. The preparation of organochromium(III) species starting from organic halides requires the use of a stoichiometric amount of chromium(II) salts or a catalytic amount of chromium(III) salts in the presence of stoichiometric reductants (such as Mn(0)). Recently, radicals formation from readily available alkenes, followed by their trapping with stoichiometric or catalytic amount of chromium(II) salts were reported in photoredox conditions for the generation of Cr(III) organometallic species. In this paper we disclose a real Nozaki‐Hiyama reaction (NH) in which photoredox conditions enable the preparation of Cr(III) allyl reagents starting from available allyl halides and stable Cr(III) salts.

Topics & Concepts

ChemistryNucleophileChromiumCatalysisStoichiometryChemoselectivityPhotoredox catalysisHalideReagentOrganic synthesisOrganic chemistryRadicalPhotocatalysisRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques
A Photoredox Nozaki‐Hiyama Reaction Catalytic in Chromium | Litcius