28115-04-0Relevant academic research and scientific papers
Electrochemical [4+2] Annulation-Rearrangement-Aromatization of Styrenes: Synthesis of Naphthalene Derivatives
Ma, Yueyue,Lv, Jufeng,Liu, Chengyu,Yao, Xiantong,Yan, Guoming,Yu, Wei,Ye, Jinxing
, p. 6756 - 6760 (2019)
We report the first electrochemical strategy to synthesize functionalized naphthalene derivatives through [4+2] annulation—rearrangement–aromatization from styrenes under mild conditions. The electrolysis does not require metals, oxidants and high valence substrates, indicating the atom and step-economy ideals. The dehydrodimer produced through [4+2] cycloaddition of 4-methoxy α-methyl styrene is isolated and proved to be the key intermediate for the following oxydehydrogenation to form carbon cation, which undergoes rearrangement–aromatization to afford the final products. This reaction represents a powerful access to construct multi-substituted naphthalene blocks in a single step.
Lewis Acid Catalyzed Transfer Hydromethallylation for the Construction of Quaternary Carbon Centers
Walker, Johannes C. L.,Oestreich, Martin
supporting information, p. 15386 - 15389 (2019/10/28)
The design and gram-scale synthesis of a cyclohexa-1,4-diene-based surrogate of isobutene gas is reported. Using the highly electron-deficient Lewis acid B(C6F5)3, application of this surrogate in the hydromethallylation of electron-rich styrene derivatives provided sterically congested quaternary carbon centers. The reaction proceeds by C(sp3)?C(sp3) bond formation at a tertiary carbenium ion that is generated by alkene protonation. The possibility of two concurrent mechanisms is proposed on the basis of mechanistic experiments using a deuterated surrogate.
Enantiopure C1-symmetric bis(imino)pyridine cobalt complexes for asymmetric alkene hydrogenation
Monfette, Sebastien,Turner, Zoe R.,Semproni, Scott P.,Chirik, Paul J.
, p. 4561 - 4564 (2012/04/23)
Enantiopure C1-symmetric bis(imino)pyridine cobalt chloride, methyl, hydride, and cyclometalated complexes have been synthesized and characterized. These complexes are active as catalysts for the enantioselective hydrogenation of geminal-disubstituted olefins.
One-pot synthesis of substituted styrenes from vicinal dibromoalkanes and arylboronic acids
Tikhonov,Vasil'ev,Chirskaya,Struchkova,Merkulova,Zlotin
, p. 122 - 129 (2008/02/08)
Dehydrobromination of vicinal dibromoalkanes in systems comprising 1,2-dimethoxy-ethane, N-butyl-N′-methylimidazolium tetrafluoroborate (or tetrabutylammonium bromide), and a base with subsequent palladium-catalyzed cross-coupling of the thus formed bromoalkenes with arylboronic acids furnished substituted styrenes. Springer Science+Business Media, Inc. 2007.
Stannous chloride dihydrate: A new catalyst for the tetrahydropyranylation of alcohols
Joju Davis,Bhalerao,Vittal Rao
, p. 1679 - 1686 (2007/10/03)
Catalytic Stannous chloride dihydrate in polar aprotic solvents like chloroform efficiently catalyse the tetrahydropyranylation of alcohols in a short time under mild conditions.
Studies in Decarboxylation. Part 16. Steric Inhibition of Resonance in a 1,5-Sigmatropic Reaction
al-Borno, Amal,Bigley, David B.
, p. 1311 - 1312 (2007/10/02)
The rates of gas-phase decarboxylation of some 3-phenyl-substituted but-3-enoic acids are best rationalized in terms of steric inhibition of resonance in the more sterically crowded members.
