1350468-22-2Relevant 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.
Palladium-catalyzed heck-type cross-couplings of unactivated alkyl iodides
McMahon, Caitlin M.,Alexanian, Erik J.
supporting information, p. 5974 - 5977 (2014/06/10)
A palladium-catalyzed, intermolecular Heck-type coupling of alkyl iodides and alkenes is described. This process is successful with a variety of primary and secondary unactivated alkyl iodides as reaction partners, including those with hydrogen atoms in t
Palladium-catalyzed heck-type reactions of alkyl iodides
Bloome, Kayla S.,McMahen, Rebecca L.,Alexanian, Erik J.
supporting information; experimental part, p. 20146 - 20148 (2012/02/01)
A palladium-catalyzed Heck-type reaction of unactivated alkyl iodides is described. This process displays broad substrate scope with respect to both alkene and alkyl iodide components and provides efficient access to a variety of cyclic products. The reaction is proposed to proceed via a hybrid organometallic-radical mechanism, facilitating the Heck-type process with alkyl halide coupling partners. Initial intermolecular studies are also reported, demonstrating the potentially wide applicability of this approach in synthesis.
