title: Ni(II)/BINOL-catalyzed alkenylation of unactivated C(sp(3))-H bonds.
abstract: The first nickel-catalyzed alkenylation of unactivated C(sp(3))-H bonds with vinyl iodides is described. The catalytic system comprises an inexpensive and air-stable Ni(acac)2 as the catalyst and BINOL as the ligand, which is highly efficient for the alkenylation of β-methyl C(sp(3))-H bonds of a broad range of aliphatic carboxamides. The resulting olefins can serve as versatile handles for further preparation. Additionally, we also demonstrated the synthesis of functionalized carboxamides bearing α-quaternary carbon centers from simple pivalamide via nickel-catalyzed sequential C(sp(3))-H bond functionalization.
authors: Department of Chemistry, Zhejiang University, Hangzhou 310027, China. bfshi@zju.edu.cn.
authors: Yue-Jin
authors: YJ
authors: Liu
authors: Zhuo-Zhuo
authors: ZZ
authors: Zhang
authors: Sheng-Yi
authors: SY
authors: Yan
authors: Yan-Hua
authors: YH
authors: Liu
authors: Bing-Feng
authors: BF
authors: Shi
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D008024:Ligands; D008968:Molecular Conformation; D009284:Naphthols / Q000737:chemistry*; D009532:Nickel / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry
chemical_list: D000475:Alkenes; D000480:Alkynes; C406944:BINOL, naphthol; D008024:Ligands; D009284:Naphthols; D009942:Organometallic Compounds; D014753:Vinyl Compounds; C569210:vinyl iodide; D009532:Nickel