125315-91-5Relevant academic research and scientific papers
Regio- And Stereoselective Hydroiodination of Internal Alkynes with Ex Situ-Generated HI
Nozawa-Kumada, Kanako,Noguchi, Koto,Akada, Tomoya,Shigeno, Masanori,Kondo, Yoshinori
supporting information, p. 6659 - 6663 (2021/09/08)
Herein, we report an efficient and practical hydroiodination of internal alkynes using HI generated ex situ from the readily available triethylsilane and I2. This system offers high regio- and stereoselectivity to afford (E)-vinyl iodides in good yields under mild conditions. Furthermore, the hydroiodination reaction shows high functional group tolerance toward alkyl, methoxy, halogen, trifluoromethyl, cyano, ester, halomethyl, acid-sensitive silyl ether, and acetal moieties.
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.
Stereospecific alkenylation of C-H bonds via reaction with β- heteroatom-functionalized trisubstituted vinyl triflones
Xiang, Jason,Jiang, Wanlong,Gong, Jianchun,Fuchs
, p. 4123 - 4129 (2007/10/03)
Aryl and alkyl β-heteroatom-trisubstituted vinyl triflones react with THF and cyclohexane to undergo trifluoromethyl radical-mediated C-H functionalization reactions to afford E and Z β-heteroatom-trisubstituted olefins. Most reactions proceed with both high yield and high stereospecificity (retention of configuration). β-Substituents which have been employed in this study are iodine, bromine, fluorine, benzoate, ethylcarbonate, and phthalimide. β-Substituents bearing powerful electron- releasing groups such as alkoxy or amino render the vinyl triflone unreactive.
TRIETHYLBORANE-INDUCED RADICAL ADDITION OF ALKYL IODIDES TO ACETYLENES
Ichinose, Yoshifumi,Matsunaga, Shin-ichiro,Fugami,Keigo,Oshima, Koichiro,Utimoto, Kiitiro
, p. 3155 - 3158 (2007/10/02)
Treatment of terminal acetylenes (R1CCH) with secondary or tertiary alkyl iodides (R2I) in the presence of triethylborane provides the corresponding alkenyl iodides (R1C(I)=CHR2) in good yields.
