29518-72-7Relevant articles and documents
16-Electron Nickel(0)-Olefin Complexes in Low-Temperature C(sp2)-C(sp3) Kumada Cross-Couplings
Lutz, Sigrid,Nattmann, Lukas,N?thling, Nils,Cornella, Josep
, p. 2220 - 2230 (2021/05/07)
Investigations into the mechanism of the low-temperature C(sp2)-C(sp3) Kumada cross-coupling catalyzed by highly reduced nickel-olefin-lithium complexes revealed that 16-electron tris(olefin)nickel(0) complexes are competent catalysts for this transformation. A survey of various nickel(0)-olefin complexes identified Ni(nor)3as an active catalyst, with performance comparable to that of the previously described Ni-olefin-lithium precatalyst. We demonstrate that Ni(nor)3, however, is unable to undergo oxidative addition to the corresponding C(sp2)-Br bond at low temperatures (a nickel(0)-alkylmagnesium complex. We demonstrate that this unique heterobimetallic complex is now primed for reactivity, thus cleaving the C(sp2)-Br bond and ultimately delivering the C(sp2)-C(sp3) bond in high yields.
Enantio- and Regioselective NiH-Catalyzed Reductive Hydroarylation of Vinylarenes with Aryl Iodides
He, Yuli,Liu, Chuang,Yu, Lei,Zhu, Shaolin
supporting information, p. 21530 - 21534 (2020/10/02)
A highly enantio- and regioselective hydroarylation process of vinylarenes with aryl halides has been developed using a NiH catalyst and a new chiral bis imidazoline ligand. A broad range of structurally diverse, enantioenriched 1,1-diarylalkanes, a structure found in a number of biologically active molecules, have been obtained with excellent yields and enantioselectivities under extremely mild conditions.
Oxygenation of Simple Olefins through Selective Allylic C?C Bond Cleavage: A Direct Approach to Cinnamyl Aldehydes
Liu, Jianzhong,Wen, Xiaojin,Qin, Chong,Li, Xinyao,Luo, Xiao,Sun, Ao,Zhu, Bencong,Song, Song,Jiao, Ning
supporting information, p. 11940 - 11944 (2017/09/20)
A novel metal-free allylic C?C σ-bond cleavage of simple olefins to give valuable cinnamyl aldehydes is reported. 1,2-Aryl or alkyl migration through allylic C?C bond cleavage occurs in this transformation, which is assisted by an alkyl azide reagent. This method enables O-atom incorporation into simple unfunctionalized olefins to construct cinnamyl aldehydes. The reaction features simple hydrocarbon substrates, metal-free conditions, and high regio- and stereoselectivity.