Synlett, Inhaltsverzeichnis Synlett DOI: 10.1055/a-2310-0880 letter Ligand-Promoted Palladium-Catalyzed β-C(sp3)–H Arylation of Ketones Using Acetohydrazide as a Transient Directing Group Kai Jia‡ , Junjie Wang‡ , Xuan Wang , Chao Jiang ∗ Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract A palladium-catalyzed β-C(sp3)–H arylation of aliphatic ketones by using acetohydrazide as a transient directing group has been developed. The reaction proceeds through a less-favored [5,5]-bicyclic palladacycle intermediate and is promoted by a pyridine ligand. Key word Key wordC–H arylation - transient directing group - acetohydrazides - ketones - palladium catalysis - pyridines Volltext Referenzen References and Notes For reviews, see: 1a Majumdar P, Pati A, Patra M, Behera RK, Behera AK. Chem. Rev. 2014; 114: 2942 1b Lei J, Xie W, Li J, Wu Y, Xie X. Eur. J. Org. 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The crude reaction mixture was purified by column chromatography (silica gel, hexanes–EtOAc (10:1)] to give a colorless oil; yield: 46%. 1H NMR [500 MHz, CDCl3): δ = 7.56 (d, J = 7.7 Hz, 2 H), 7.25 (d, J = 7.5 Hz, 2 H), 2.97 (dd, J = 13.2, 8.2 Hz, 1 H), 2.73 (ddd, J = 19.2, 13.3, 6.4 Hz, 2 H), 2.03 (s, 3 H), 1.66 (dt, J = 21.7, 7.2 Hz, 1 H), 1.52 (dt, J = 17.2, 5.3 Hz, 1 H), 0.91 (t, J = 7.4 Hz, 3 H). 13C NMR (126 MHz, CDCl3): δ = 211.0, 145.6, 132.2, 129.7, 118.8, 110.3, 55.5, 36.9, 30.1, 24.6, 11.3. HRMS (ESI-TOF): m/z calcd [M + H]+ for C13H16NO: 202.2768; found: 202.2765.§ 13 Li Y.-H, Ouyang Y, Chekshin N, Yu J.-Q. ACS Catal. 2022; 12: 10581 Zusatzmaterial Zusatzmaterial Supporting Information
