558-22-5Relevant articles and documents
Kukolich et al.
, p. 33,36, 37 (1971)
1,2-(Bis)trifluoromethylation of Alkynes: A One-Step Reaction to Install an Underutilized Functional Group
Guo, Shuo,AbuSalim, Deyaa I.,Cook, Silas P.
, p. 11704 - 11708 (2019)
Modifying the electronic properties of olefins is the quintessential approach to tuning alkene reactivity. In this context, the exploration of trifluoromethyl groups as divergent electronic modifiers has not been considered. In this work, we describe a copper-mediated 1,2-(bis)trifluoromethylation of acetylenes to create E-hexafluorobutenes (E-HFBs) under blue light in a single step. The reaction proceeds with high yield and E/Z selectivity. Since the alkyne captures two trifluoromethyl groups from each molecule of bpyCu(CF3)3, mechanistic studies were conducted to illuminate the role of the reactants. Interestingly, E-HFBs exhibit remarkable stability to standard olefin functionalization reactions in spite of the pendant trifluoromethyl groups. This finding has significant implications for medicine, agroscience, and materials.
Ruoff et al.
, p. 1359 (1971)
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Polo,Wilson
, p. 1129 (1953)
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Carbon-Carbon Bond-Forming Reductive Elimination from Isolated Nickel(III) Complexes
Bour, James R.,Camasso, Nicole M.,Meucci, Elizabeth A.,Kampf, Jeff W.,Canty, Allan J.,Sanford, Melanie S.
supporting information, p. 16105 - 16111 (2016/12/22)
This manuscript describes the design, synthesis, characterization, and reactivity studies of organometallic NiIII complexes of general structure TpNiIII(R)(R1) (Tp = tris(pyrazolyl)borate). With appropriate selection of th
Nucleophile-catalyzed, facile, and highly selective C-H activation of fluoroform with Pd(II)
Takemoto, Shin,Grushin, Vladimir V.
supporting information, p. 16837 - 16840 (2013/12/04)
Exceedingly facile (23 C) and chemoselective H-CF3 activation with [(dppp)Pd(Ph)(OH)] in the presence of a Lewis base promoter such as n-Bu3P leads to Pd-CF3 bond formation in nearly quantitative yield. A combined experimental and computational study points to a new mechanism that involves H-bonding Pd-O(H)···H-CF 3 and nucleophilic attack of the promoter on the metal, followed by a push-pull-type collapse of the resultant five-coordinate Pd(II) intermediate via a polar transition state.