Nickel-Catalyzed Regioselective Alkenylarylation of γ,δ-Alkenyl Ketones via Carbonyl Coordination.

Autor: Dhungana RK; Department of Chemistry, Pennsylvania State University, University Park, PA, 16802, USA., Aryal V; Department of Chemistry, Pennsylvania State University, University Park, PA, 16802, USA., Niroula D; Department of Chemistry, Pennsylvania State University, University Park, PA, 16802, USA., Sapkota RR; Department of Chemistry, Pennsylvania State University, University Park, PA, 16802, USA., Lakomy MG; Department of Chemistry, Pennsylvania State University, University Park, PA, 16802, USA., Giri R; Department of Chemistry, Pennsylvania State University, University Park, PA, 16802, USA.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2021 Aug 23; Vol. 60 (35), pp. 19092-19096. Date of Electronic Publication: 2021 Jul 20.
DOI: 10.1002/anie.202104871
Abstrakt: We disclose a nickel-catalyzed reaction, which enabled us to difunctionalize unactivated γ,δ-alkenes in ketones with alkenyl triflates and arylboronic esters. The reaction was made feasible by the use of 5-chloro-8-hydroxyquinoline as a ligand along with NiBr 2 ⋅DME as a catalyst and LiOtBu as base. The reaction proceeded with a wide range of cyclic, acyclic, endocyclic and exocyclic alkenyl ketones, and electron-rich and electron-deficient arylboronate esters. The reaction also worked with both cyclic and acyclic alkenyl triflates. Control experiments indicate that carbonyl coordination is required for the reaction to proceed.
(© 2021 Wiley-VCH GmbH.)
Databáze: MEDLINE
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