Two mixed ligand copper(I) complexes, [Cu(PPh3)3(k-O-mand)] (CuP3M) and [Cu(PPh3)2(k2-O,O’-mand)] (CuP2M) (mand=dlmandelate) were synthesized and fully characterized. The different coordination modes of the α-hydroxycarboxylate ligand in CuP2M and CuP3M are clearly demonstrated by infrared spectroscopy, with the asymmetric νC=O stretching being observed at 1626 (CuP3M) and 1593 (CuP2M) cm 1, respectively. Solution NMR studies (1H, 31P{1H}), elemental and X-ray structure analyses confirmed the nature of the synthesized compounds. Complexes CuP2M and CuP3M were in carbene transfer reactions towards unsaturated bonds, using ethyl diazoacetate (N2CHCOOEt, EDA) as carbene source. Indeed, they promoted the trans-diastereoselective cyclopropanation of terminal and internal olefins under mild reaction conditions and low catalyst loading (1% mol).

Mixed‐Ligand Mandelato‐Phosphine Copper(I) Complexes as Active Catalysts in Carbene Transfer Reactions

Cinco, Anita
Membro del Collaboration Group
;
Colombo, Gioele
Writing – Original Draft Preparation
;
Brenna, Stefano
Supervision
;
Ardizzoia, G. Attilio
Supervision
2022

Abstract

Two mixed ligand copper(I) complexes, [Cu(PPh3)3(k-O-mand)] (CuP3M) and [Cu(PPh3)2(k2-O,O’-mand)] (CuP2M) (mand=dlmandelate) were synthesized and fully characterized. The different coordination modes of the α-hydroxycarboxylate ligand in CuP2M and CuP3M are clearly demonstrated by infrared spectroscopy, with the asymmetric νC=O stretching being observed at 1626 (CuP3M) and 1593 (CuP2M) cm 1, respectively. Solution NMR studies (1H, 31P{1H}), elemental and X-ray structure analyses confirmed the nature of the synthesized compounds. Complexes CuP2M and CuP3M were in carbene transfer reactions towards unsaturated bonds, using ethyl diazoacetate (N2CHCOOEt, EDA) as carbene source. Indeed, they promoted the trans-diastereoselective cyclopropanation of terminal and internal olefins under mild reaction conditions and low catalyst loading (1% mol).
https://chemistry-europe.onlinelibrary.wiley.com/hub/journal/23656549/overview
copper; mandelato ligand; homogeneous catalysis; cyclopropanation; olefins
Cinco, Anita; Colombo, Gioele; Brenna, Stefano; Therrien, Bruno; Ardizzoia, G. Attilio
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11383/2138471
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