127462-39-9Relevant academic research and scientific papers
Z -selective olefin synthesis via iron-catalyzed reductive coupling of alkyl halides with terminal arylalkynes
Cheung, Chi Wai,Zhurkin, Fedor E.,Hu, Xile
supporting information, p. 4932 - 4935 (2015/05/05)
Selective catalytic synthesis of Z-olefins has been challenging. Here we describe a method to produce 1,2-disubstituted olefins in high Z selectivity via reductive cross-coupling of alkyl halides with terminal arylalkynes. The method employs inexpensive and nontoxic catalyst (iron(II) bromide) and reductant (zinc). The substrate scope encompasses primary, secondary, and tertiary alkyl halides, and the reaction tolerates a large number of functional groups. The utility of the method is demonstrated in the synthesis of several pharmaceutically relevant molecules. Mechanistic study suggests that the reaction proceeds through an iron-catalyzed anti-selective carbozincation pathway.
TRANSITION METAL ?-COMPLEXES IN ORGANIC SYNTHESIS 5. CROSS-COUPLING OF ORGANOMANGANESE COMPOUNDS WITH ALKENYL IODIDES
Kasatkin, A. N.,Romanova, T. Yu.,Tsypyshev, O. Yu.,Tolstikov, G. A.,Lomakina, S. I.
, p. 2410 - 2415 (2007/10/02)
Aryl organomanganese compounds ArMnX and Ph3MnLi (Ar = Ph, p-MeC6H4, p-MeOC6H4, p-ClC6H4, p-BrC6H4, α-naphthyl; X = Cl, Br) react with alkenyl iodides RR1C=CR2I (R = H, Pr, Bu, i-Bu, C6H13, CH2=CHCH2, Ph; R1 = H, Pr, C5H11; R2 = H, Pr, SiMe3) in THF at 0-20 deg C to give cross-coupling products RR1C=CR2Ar in high yields.
