88787-20-6Relevant academic research and scientific papers
Catalytic Regioselective Olefin Hydroarylation(alkenylation) by Sequential Carbonickelation-Hydride Transfer
Liu, Chen-Fei,Luo, Xiaohua,Wang, Hongyu,Koh, Ming Joo
supporting information, p. 9498 - 9506 (2021/07/19)
Alkene hydrocarbofunctionalization represents one of the most important classes of chemical transformations, but related branched-selective examples with unactivated olefins are scarce. Here, we report that catalytic amounts of a dimeric Ni(I) complex and an exogenous alkoxide base promote Markovnikov-selective hydroarylation(alkenylation) of unactivated and activated olefins using organo bromides or triflates derived from widely available phenols and ketones. Products bearing aryl- and alkenyl-substituted tertiary and quaternary centers could be isolated in up to 95% yield and >99:1 regioisomeric ratios. Contrary to previous dual-catalytic methods that rely on metal-hydride atom transfer (MHAT) to the olefin prior to carbofunctionalization with a cocatalyst, our mechanistic evidence points toward a nonradical reaction pathway that begins with site-selective carbonickelation across the C═C bond followed by hydride transfer using alkoxide as the hydride source. Utility of the single-catalyst protocol is highlighted through the synthesis of medicinally relevant scaffolds.
CROSS-COUPLING OF ALLYL COMPOUNDS WITH ORGANOZINC HALIDE REAGENTS CATALYSED BY TRANSITION-METAL COMPLEXES
Minsker, D. L.,Ibragimov, A. G.,Dzhemilev, U. M.
, p. 873 - 875 (2007/10/02)
A simple and promising method is proposed for the production of unsaturated hydrocarbons with a given structure by the cross-coupling of allyl- and benzylzinc bromides with allyl ethers and esters and allyl sulfones under the influence of palladium and nickel comlexes with had been modified by electron-donating ligands and were soluble in organic solvents.The effects of the nature and the structure of the catalyst components and also of the reaction conditions on the yield and direction of the cross-coupling reaction were investigated.
