Working Paper Review Version 1 This version is not peer-reviewed

C,C- and C,N-Chelated Organocopper Compounds

Version 1 : Received: 1 September 2021 / Approved: 2 September 2021 / Online: 2 September 2021 (12:01:01 CEST)

How to cite: Liu, L.; Chen, H.; Yang, Z.; Wei, J.; Xi, Z. C,C- and C,N-Chelated Organocopper Compounds. Preprints 2021, 2021090036 Liu, L.; Chen, H.; Yang, Z.; Wei, J.; Xi, Z. C,C- and C,N-Chelated Organocopper Compounds. Preprints 2021, 2021090036

Abstract

Copper-catalyzed and organocopper-involved reactions are of great significance in organic synthesis. To have a deep understanding of the reaction mechanisms, the structural characterizations of organocopper intermediates become indispensable. Meanwhile, the structure-function relationship of organocopper compounds would advance rational design and development of new Cu-based reactions and organocopper reagents. Compared to the mono-carbonic ligand, the C,N- and C,C-bidentate ligands better stabilize the unstable organocopper compounds. The bidentate ligands can chelate to the same copper atom via ?2-mode, forming a mono-cupra-cyclic compounds with at least one acute C-Cu-C angle. When the bidentate ligands bind to two copper atoms via ?1-mode at each coordinating site, the bimetallic macrocyclic compounds will form nearly linear C-Cu-C angles. The anionic coordinating sites of the bidentate ligand can also bridge two metals via ?2-mode, forming organocopper aggregates with Cu-Cu interactions and organocuprates with contact ion pair structures. The reaction chemistry of some selected organocopper compounds is highlighted, showing their unique structure-reactivity relationships.

Keywords

organocopper; C,N-chelated; C,C-chelated; bidentate; butadienyl; intramolecular coordination; three center-two electron bonds; structure-reactivity relationship

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