806-58-6Relevant academic research and scientific papers
A new titanium tetrachloride mediated annulation of α -aryl-substituted carbonyl compounds with alkynes: A simple and highly efficient method for the regioselective synthesis of polysubstituted naphthalene derivatives
Kabalka, George W.,Ju, Yuhong,Wu, Zhongzhi
, p. 7915 - 7917 (2003)
A new straightforward procedure has been developed for the synthesis of polysubstituted naphthalene derivatives. The reaction of α -aryl-substituted carbonyl compounds with terminal or internal alkynes in the presence of TiCl4 regioselectively generates substituted naphthalene derivatives in good to excellent yields.
A new route for the thermal isomerization of a highly substituted hexadienyne derivative
Berger, Harald,Hopf, Henning,Dix, Ina,Jones, Peter G.
, p. 3401 - 3403 (2004)
Whereas the thermal isomerization of perphenylbutenyne (11) at 290 °C in toluene leads to the benzannelated semibullvalene derivative 13, pyrolysis at 360 °C furnishes the triphenylnaphthalene 12. The mechanisms of both cycloisomerizations, which presumably proceed via the isobenzene intermediate 14, are discussed. The structure of the rearrangement product 13 was proven by single-crystal X-ray analysis. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
Direct Synthesis of Napthalenes by Nickel-Catalyzed Cascade Cyclization of o-Vinyl Chlorobenzenes with Internal Alkynes
Liang, Guanfeng,Lin, Jin,Tian, Xu,Wu, Chaoyi
supporting information, p. 6764 - 6767 (2021/12/31)
An efficient nickel-catalyzed arylnickelation of alkyne/Heck cyclization of challenging o-vinyl chlorobenzenes with internal alkynes has been developed. This protocol enables synthesis of a wide variety of substituted naphthalenes in a cascade process from readily available starting materials. Mechanistic studies indicate the radical pathway is not involved in the cascade catalytic system.
Synthesis, C-H bond functionalisation and cycloadditions of 6-styryl-1,2-oxathiine 2,2-dioxides
Gabbutt, Christopher D.,Heron, B. Mark,Lilly, Thomas,Ogwang, Ochola W.,Zonidis, Dimitrios
, p. 6431 - 6446 (2021/08/03)
A series of 6-styryl-1,2-oxathiine 2,2-dioxides have been efficiently obtained by a two-step protocol from readily available (1E,4E)-1-(dimethylamino)-5-arylpenta-1,4-dien-3-ones involving a regioselective sulfene addition and subsequent Cope elimination. Pd-Mediated direct C-H bond functionalisation of the 6-styryl-1,2-oxathiine 2,2-dioxides and a wider selection of 5,6-diaryl substituted 1,2-oxathiine 2,2-dioxides proceeded smoothly to afford C-3 (hetero)aryl substituted analogues and the results are contrasted with those of a complementary bromination - Suzuki cross-coupling sequence. Whilst the cycloaddition of benzyne, derived fromin situfluoride initiated decomposition of 2-(trimethylsilyl)phenyl trifluoromethanesulfonate, to the substituted 1,2-oxathiine 2,2-dioxides resulted in low yields of substituted naphthalenes, the addition of 4-phenyl-1,2,4-triazoline-3,5-dione to the 6-styryl-1,2-oxathiine 2,2-dioxides afforded novel 5,9-dihydro-1H-[1,2]oxathiino[5,6-c][1,2,4]triazolo[1,2-a]pyridazine-1,3(2H)-dione 8,8-dioxides through a silica-mediated isomerisation of the initial [4 + 2] adducts.
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
supporting information, p. 6756 - 6760 (2019/04/17)
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.
Gold(I)-catalyzed double migration cascades toward (1E,3E)-dienes and naphthalenes
Dudnik, Alexander S.,Schwier, Todd,Gevorgyan, Vladimir
experimental part, p. 1859 - 1870 (2009/07/04)
A novel gold(I)-catalyzed cascade cycloisomerization of a variety of propargylic esters leading to unsymmetrically substituted naphthalenes has been developed. This domino process involves an unprecedented tandem sequence of 1,3- and 1,2-migrations of two
Gold-catalyzed double migration-benzannulation cascade toward naphthalenes
Dudnik, Alexander S.,Schwier, Todd,Gevorgyan, Vladimir
supporting information; experimental part, p. 1465 - 1468 (2009/04/10)
(Chemical Equation Presented) A novel gold(I)-catalyzed cycloisomerization of propargylic esters leading to unsymmetrically substituted naphthalenes has been developed. This cascade reaction involves an unprecedented tandem sequence of 1,3- and 1,2-migration of two different migrating groups. It is believed that this transformation likely proceeds via the formation of 1,3-diene intermediate or its precursor, which upon cyclization and aromatization steps transforms into the naphthalene core. 2008 American Chemical Society.
Copper-catalyzed electrosynthesis of 1-acyl-2,2-diphenylcyclopropanes and their behaviour in acidic medium
Oudeyer, Sylvain,Léonel, Eric,Paugam, Jean Paul,Nédélec, Jean-Yves
, p. 1073 - 1081 (2007/10/03)
The formation of 1-acyl-2,2-diphenylcyclopropanes is performed under mild electrochemical conditions. These cyclopropane derivatives, through acid-catalyzed ring-opening, lead to γ,γ-diphenyl-β,γ-unsaturated carbonyl compounds which evolve into either substituted naphthalenes, or β-benzhydryl-α,β-cycloalkenones depending on the acyclic or cyclic nature of the intermediate allyl ketone.
Palladium-Catalyzed Annulation of Internal Alkynes by Arene-Containing Vinylic Iodides and Triflates
Larock, Richard C.,Tian, Qingping
, p. 2002 - 2009 (2007/10/03)
In the presence of a palladium catalyst, internal alkynes undergo carboannulation by cyclic and acyclic vinylic iodides and triflates bearing a neighboring aromatic ring to produce a variety of carbocycles. For example, a number of 9,10-disubstituted-1,2,3,4-tetrahydrophenanthrenes have been prepared in good yields through the palladium-catalyzed annulation of internal alkynes by 2-phenyl-1-cyclohexenyl triflate (1) or l-iodo-2-phenylcyclohexene (2). This annulation process is fairly general and highly regioselective. The process appears to involve oxidative addition of the vinylic substrate to Pd(0) to produce a vinylic palladium intermediate, which adds the carbon moiety to the less hindered end and the palladium to the more hindered end of the alkyne, followed by intramolecular ring closure onto the neighboring aryl group. The scope and limitations of this methodology are discussed.
