7302-00-3Relevant articles and documents
Asymmetric Grignard cross-coupling reaction between (E)-β-bromostyrene and 1-phenylethylmagnesium chloride
Kreuzfeld, H.-J.,Doebler, Chr.,Abicht, H.-P.
, p. 287 - 292 (1987)
Trans-2,3-bis-(diphenylphosphinomethyl)-norbornene-(5), trans-2,3-bis-(diphenylphosphinomethyl)-7-oxanorbornane, and (-)-/2((S)-1-dimethylaminoethyl)phenyl/-diphenylphosphine have been used as ligands for the nickel and palladium catalyzed asymmetric Grignard cross-coupling reaction giving the coupling product (E)-1,3-diphenyl-1-butene.Chemical yields from 60 to 95percent and optical yields up to 40percent were obtained, depending on the types of ligand coordinated.
Nickel-Catalyzed Arylation of C(sp3)-O Bonds in Allylic Alkyl Ethers with Organoboron Compounds
Li, Xiaowei,Li, Yuxiu,Zhang, Zhong,Shi, Xiaolin,Liu, Ruihua,Wang, Zemin,Li, Xiangqian,Shi, Dayong
supporting information, p. 6612 - 6616 (2021/09/02)
A nickel-catalyzed cross-coupling of allylic alkyl ethers with organoboron compounds through the cleavage of the inert C(sp3)-O(alkyl) bonds is described. Several types of allylic alkyl ethers can be coupled with various boronic acids or their derivatives to give the corresponding products in good to excellent yields with wide functional group tolerance and excellent regioselectivity. The gram-scale reaction and late-stage modification of biologically active compounds further prove the practicality of this synthetic method.
Nickel-Catalyzed Hydroarylation of in Situ Generated 1,3-Dienes with Arylboronic Acids Using a Secondary Homoallyl Carbonate as a Surrogate for the 1,3-Diene and Hydride Source
Hamaguchi, Takashi,Kawatsura, Motoi,Takahashi, Yoshiyuki,Tsuji, Hiroaki
, (2020/02/15)
The nickel-catalyzed hydroarylation of 1,3-dienes with arylboronic acids using a secondary homoallyl carbonate as a surrogate for the 1,3-diene and hydride source has been developed. The synthetic strategy allowed an efficient access to a wide array of hydroarylation products in high yields with high functional group compatibility without the use of an external hydride source. Mechanistic experiments indicated that the alkene-directed oxidative addition and subsequent β-hydride elimination would be a critical process in this transformation.