79958-52-4Relevant articles and documents
Cu-mediated or metal-free alkylation of gem-dibromoalkenes with tertiary, secondary and primary alkyl Grignard reagents
Deng, Yupian,Zhang, Xuxue,Liu, Chuan,Cao, Song
, (2021/01/18)
A novel copper-mediated or transition-metal-free alkylation of gem-dibromoalkenes with tertiary, secondary and primary alkyl Grignard reagents was described. The outcomes of these reactions were found to be highly dependent on the reaction conditions and
Diastereodivergent Reductive Cross Coupling of Alkynes through Tandem Catalysis: Z- and E-Selective Hydroarylation of Terminal Alkynes
Armstrong, Megan K.,Goodstein, Madison B.,Lalic, Gojko
, p. 10233 - 10241 (2018/08/23)
A diastereodivergent hydroarylation of terminal alkynes is accomplished using tandem catalysis. The hydroarylation allows highly selective synthesis of both E and Z diastereoisomers of aryl alkenes, from the same set of starting materials, using the same combination of palladium and copper catalysts. The selectivity is controlled by simple changes in the stoichiometry of the alcohol additive. The hydroarylation has excellent substrate scope and can be accomplished in the presence of various classes of compounds, including esters, nitriles, alkyl halides, epoxides, carbamates, acetals, ethers, silyl ethers, and thioethers. The Z-selective hydroarylation is accomplished using a new approach based on tandem Sonogashira coupling and catalytic semireduction. The E-selective hydroarylation involves an additional catalytic isomerization of the Z-alkene. Our explorations of the reaction mechanism explain the role of individual reaction components and how the subtle changes in the reaction conditions influence the rates of specific steps of the hydroarylation. Our studies also show that, although the Z- and E-selective hydroarylation reactions are mechanistically closely related, the roles of the palladium and copper catalysts in the two reactions are different.
Metal-Free Oxidative Decarbonylative Hydroalkylation of Alkynes with Secondary and Tertiary Alkyl Aldehydes
Ouyang, Xuan-Hui,Song, Ren-Jie,Liu, Bang,Li, Jin-Heng
, p. 1903 - 1909 (2016/07/06)
A new, metal-free, radical-mediated oxidative decarbonylative hydroalkylation of various alkynes with secondary and tertiary alkyl aldehydes using di-tert-butyl peroxide (DTBP) as oxidant is presented. This method enables the simultaneous formation of a C C bond and a C H bond through a sequence of decarbonylation, radical addition and protonation, and provides a straightforward route for transforming alkynes into alkenes with high compatibility with both alkynes and alkyl aldehydes. (Figure presented.) .
