Iridium-catalyzed Addition of Acid Chlorides to Terminal Alkynes
Overview
Affiliations
An iridium N-heterocyclic carbene (NHC) complex, IrCl(cod)(IPr), successfully catalyzed an addition of common aromatic acid chlorides to terminal alkynes to afford (Z)-beta-chloro-alpha,beta-unsaturated ketones regio- and stereoselectively. When the NHC ligand (IPr) was changed to a phosphine (RuPhos), the addition occurred with decarbonylation to give the corresponding (Z)-vinyl chlorides. Furthermore, the former reaction using IrCl(cod)(IPr) can be applied to the catalytic synthesis of 2,5-disubstituted furans.
The Divergent Reactivity of Acid Chlorides Under Transition Metal Catalysis.
Denton E, Stepanovic O, Morandi B Chemistry. 2024; 30(67):e202401852.
PMID: 39506462 PMC: 11610683. DOI: 10.1002/chem.202401852.
Catalytic Carbochlorocarbonylation of Unsaturated Hydrocarbons via C-COCl Bond Cleavage*.
Denton E, Lee Y, Roediger S, Boehm P, Fellert M, Morandi B Angew Chem Int Ed Engl. 2021; 60(43):23435-23443.
PMID: 34432940 PMC: 8596603. DOI: 10.1002/anie.202108818.
Tian X, Karl T, Reiter S, Yakubov S, de Vivie-Riedle R, Konig B Angew Chem Int Ed Engl. 2021; 60(38):20817-20825.
PMID: 34165861 PMC: 8518744. DOI: 10.1002/anie.202105895.
Chen F, Hua Z, Chen J, Chen J, Lee D, Xia Y Front Chem. 2021; 8:621545.
PMID: 33968892 PMC: 8100659. DOI: 10.3389/fchem.2020.621545.
Decarbonylative Suzuki-Miyaura Cross-Coupling of Aroyl Chlorides.
Zhou T, Xie P, Ji C, Hong X, Szostak M Org Lett. 2020; 22(16):6434-6440.
PMID: 32806154 PMC: 7456303. DOI: 10.1021/acs.orglett.0c02250.