57013-04-4Relevant articles and documents
Synthesis of Functionalized α-Vinyl Aldehydes from Enaminones
Chen, Jie,Guo, Pan,Zhang, Jianguo,Rong, Jiaxin,Sun, Wangbin,Jiang, Yaojia,Loh, Teck-Peng
supporting information, p. 12674 - 12679 (2019/08/07)
An efficient RhII-catalyzed synthesis of functionalized α-vinyl aldehydes with high E/Z stereoselectivity was developed. The reaction mediates the cyclopropanation of enaminones with vinyl carbenoids that are generated from cyclopropenes in situ to give the aminocyclopropane intermediates. Selective C?C bond cleavage of the cyclopropane intermediates leads to formation of α-vinyl aldehyde derivatives with high E/Z selectivity. This method proceeds at room temperature under very mild reaction conditions and works with a broad substrate scope.
Oxydifluoromethylation of Alkenes by Photoredox Catalysis: Simple Synthesis of CF2H-Containing Alcohols
Arai, Yusuke,Tomita, Ren,Ando, Gaku,Koike, Takashi,Akita, Munetaka
supporting information, p. 1262 - 1265 (2016/01/25)
We have developed a novel and simple protocol for the direct incorporation of a difluoromethyl (CF2H) group into alkenes by visible-light-driven photoredox catalysis. The use of fac-[Ir(ppy)3] (ppy=2-pyridylphenyl) photocatalyst and shelf-stable Hu's reagent, N-tosyl-S-difluoromethyl-S-phenylsulfoximine, as a CF2H source is the key to success. The well-designed photoredox system achieves synthesis of not only β-CF2H-substituted alcohols but also ethers and an ester from alkenes through solvolytic processes. The present method allows a single-step and regioselective formation of C(sp3)-CF2H and C(sp3)-O bonds from C=C moiety in alkenes, such as hydroxydifluoromethylation, regardless of terminal or internal alkenes. Moreover, this methodology tolerates a variety of functional groups. Light up the bulb! A novel and simple protocol for the direct incorporation of a difluoromethyl (CF2H) group into alkenes by visible-light-driven photoredox catalysis has been developed (see scheme). An Ir photocatalyst is useful for the generation of a CF2H radical through one-electron reduction of Hu's reagent. The present reaction system produces not only various β-CF2H-substituted alcohols, but also ethers and esters in regiospecific manners under mild conditions.
Divergent outcomes of gold(I)-catalyzed indole additions to 3,3-disubstituted cyclopropenes
Young, Paul C.,Hadfield, Maximillian S.,Arrowsmith, Lynn,MacLeod, Kristina M.,Mudd, Richard J.,Jordan-Hore, James A.,Lee, Ai-Lan
supporting information; experimental part, p. 898 - 901 (2012/04/18)
Depending on the conditions employed, gold(I)-catalyzed addition of indoles to 3,3-disubstituted cyclopropenes can be controlled to yield either 3-(E)-vinylindoles (3) or bis-indolylalkanes (4). If the cyclopropene substituents are sterically bulky, unprecedented gold-catalyzed oxidation under air occurs to yield bis-indolylalkene (5) and epoxide (6) at room temperature.