139377-71-2Relevant articles and documents
Regioselective Single-Electron Tsuji-Trost Reaction of Allylic Alcohols: A Photoredox/Nickel Dual Catalytic Approach
Wang, Zheng-Jun,Zheng, Shuai,Romero, Eugénie,Matsui, Jennifer K.,Molander, Gary A.
supporting information, p. 6543 - 6547 (2019/08/26)
A radical-mediated functionalization of allyl alcohol derived partners with a variety of alkyl 1,4-dihydropyridines via photoredox/nickel dual catalysis is described. This transformation transpires with high linear and E-selectivity, avoiding the requirement of harsh conditions (e.g., strong base, elevated temperature). Additionally, using aryl sulfinate salts as radical precursors, allyl sulfones can also be obtained. Kinetic isotope effect experiments implicated oxidative addition of the nickel catalyst to the allylic electrophile as the turnover-limiting step, supporting previous computational studies.
Hydroalkylation of terminal aryl alkynes with alkyl diacyl peroxides
Li, Yougui,Ge, Liang,Qian, Bo,Babu, Kaki Raveendra,Bao, Hongli
supporting information, p. 5677 - 5680 (2016/11/28)
A photo and nickel co-catalyzed hydroalkylation of terminal aryl alkynes enabled Z-preferred olefin synthesis has been developed under mild conditions. Alkyl diacyl peroxides were utilized as a new type of alkylation reagents and afforded Z-olefins as the major products in moderate to good yields.
Novel nickel-catalyzed coupling reaction of allyl ethers with chlorosilanes, alkyl tosylates, or alkyl halides promoted by vinyl-Grignard reagent leading to allylsilanes or alkenes
Terao, Jun,Watabe, Hiroyasu,Watanabe, Hiroyuki,Kambe, Nobuaki
, p. 1674 - 1678 (2007/10/03)
A new method for a carbon-silicon or carbon-carbon bond forming reaction between allyl ethers and chlorosilanes, alkyl tosylates, or alkyl halides giving rise to allylsilanes or alkenes has been developed. This reaction proceeds efficiently at ambient temperature by the combined use of nickel catalysts and a vinyl-Grignard reagent. A possible reaction pathway involving the formation of allyl-Grignard reagents via transmetallation of π-allylnickel complexes with the vinyl-Grignard reagent and subsequent trapping of the thus formed allyl-Grignard reagents with electrophiles is proposed.