Vinyl Thianthrenium Tetrafluoroborate: A Practical and Versatile Vinylating Reagent Made from Ethylene
The use of vinyl electrophiles in synthesis has been hampered by the lack of access to a suitable reagent that is practical and of appropriate reactivity. In this work we introduce a vinyl thianthrenium salt as an effective vinylating reagent. The bench-stable, crystalline reagent can be readily prepared from ethylene gas at atmospheric pressure in one step and is broadly useful in the annulation chemistry of (hetero)cycles, N-vinylation of heterocyclic compounds, and palladium-catalyzed cross-coupling reactions. The structural features of the thianthrene core enable a distinct synthesis and reactivity profile, unprecedented for other vinyl sulfonium derivatives.
Combining photoredox-catalyzed trifluoromethylation and oxidation with dmso: Facile synthesis of α-trifluoromethylated ketones from aromatic alkenes
Trifluoromethylated ketones are useful building blocks for organic compounds with a trifluoromethyl group. A new and facile synthesis of ketones with a trifluoromethyl substituent in the α-position proceeds through a one-pot photoredox-catalyzed trifluoromethylation-oxidation sequence of aromatic alkenes. Dimethyl sulfoxide (DMSO) serves as a key and mild oxidant under these photocatalytic conditions. Furthermore, an iridium photocatalyst, fac[Ir(ppy)3] (ppy=2-phenylpyridine), turned out to be crucial for the present photoredox process. Valuable α-CF3-substituted ketones can be synthesized from aromatic alkenes by combining photoredox-catalyzed trifluoromethylation and oxidation with DMSO. The iridium photocatalyst fac-[Ir(ppy)3] (ppy=2-phenylpyridine) plays key roles in this keto-trifluoromethylation. SET=single electron transfer.
Intermolecular aminotrifluoromethylation of alkenes by visible-light-driven photoredox catalysis
Intermolecular aminotrifluoromethylation of alkenes catalyzed by [Ru(bpy)3]2+ under visible light irradiation has been explored. The present photocatalytic protocol achieves highly efficient and regioselective difunctionalization of C=C bonds, leading to a variety of β-trifluoromethylamines. The reaction is applied to late-stage aminotrifluoromethylation of steroid and amino acid scaffolds.
Yasu, Yusuke,Koike, Takashi,Akita, Munetaka
supporting information
p. 2136 - 2139
(2013/06/05)
Rhodium-catalyzed cross-coupling of organoboron compounds with vinyl acetate
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Yu, Jung-Yi,Kuwano, Ryoichi
supporting information; experimental part
p. 7217 - 7220
(2009/12/26)
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