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.

A Photoredox Nozaki-Hiyama Reaction Catalytic in Chromium

Calogero F.;Magagnano G.;Gualandi A.;Marchini M.;Ceroni P.;Cozzi P. G.
2022

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.
2022
Calogero F.; Potenti S.; Magagnano G.; Mosca G.; Gualandi A.; Marchini M.; Ceroni P.; Cozzi P.G.
File in questo prodotto:
File Dimensione Formato  
European J Organic Chem - 2022 - Calogero - A Photoredox Nozakiâ Hiyama Reaction Catalytic in Chromium.pdf

accesso aperto

Tipo: Versione (PDF) editoriale
Licenza: Licenza per Accesso Aperto. Creative Commons Attribuzione - Non commerciale - Non opere derivate (CCBYNCND)
Dimensione 3.81 MB
Formato Adobe PDF
3.81 MB Adobe PDF Visualizza/Apri
ejoc202200350-sup-0001-misc_information.pdf

accesso aperto

Tipo: File Supplementare
Licenza: Licenza per Accesso Aperto. Creative Commons Attribuzione - Non commerciale - Non opere derivate (CCBYNCND)
Dimensione 3.33 MB
Formato Adobe PDF
3.33 MB Adobe PDF Visualizza/Apri

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/890071
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 1
  • ???jsp.display-item.citation.isi??? 2
social impact