1350843-85-4Relevant academic research and scientific papers
Palladium-catalyzed cascade decarboxylative amination/6- endo-dig benzannulation of o-alkynylarylketones with n-hydroxyamides to access diverse 1-naphthylamine derivatives
Zuo, Youpeng,He, Xinwei,Tang, Qiang,Hu, Wangcheng,Zhou, Tongtong,Shang, Yongjia
supporting information, p. 3890 - 3894 (2020/05/18)
An efficient and practical one-pot strategy to produce highly substituted 1-naphthylamines via sequential palladium-catalyzed decarboxylative amination/intramolecular 6-endo-dig benzannulation reactions has been described. In this reaction, a broad range of electron-rich, electron-neutral, and electron-deficient o-alkynylarylketones react well with N-hydroxyl aryl/alkylamides to give a diversity of 1-naphthylamines in good to excellent yields under mild reaction conditions. The gram-scale synthesis, with benefits such as undiminished product yield and easy transformation, illustrated the practicality of this method.
CuI/Cu(OTf)2/DMSO system-catalyzed intramolecular oxidative cyclization of (o-alkynyl)arylketones: Efficient synthesis of 1,4-naphthoquinones
Zhou, Bingwei,Liu, Qian,Wang, Heng,Jin, Hongwei,Liu, Yunkui
, p. 3815 - 3821 (2019/06/14)
A concise and efficient method for the synthesis of 1,4-naphthoquinones has been successfully developed involving a CuI/Cu(OTf)2/DMSO system-catalyzed intramolecular oxidative cyclization of (o-alkynyl)arylketones. The present protocol provided a novel approach to access functionalized 1,4-naphthoquinones from non-naphthoquinone precursors with good selectivity and functional group tolerance.
Chemo- and Regioselective Catalyst-Controlled Carbocyclization of Alkynyl Ketones: Rapid Synthesis of 1-Indanones and 1-Naphthols
Song, Liangliang,Tian, Guilong,Van der Eycken, Erik V.
supporting information, p. 7645 - 7648 (2019/05/21)
A catalyst-controlled intramolecular carbocyclization of 2-alkynyl aryl ketones is presented. Under rhodium(III) catalysis, 1-indanones are formed through 5-exo-dig carbocyclizations with exclusive chemo-, regio- and stereoselectivity. When catalyzed by copper(I), 1-naphthols are obtained through 6-endo-dig carbocyclizations with exclusive chemo- and regioselectivity.
Copper-Catalyzed Cascade Cyclization of Arylsulfonylhydrazones Derived from ortho-Alkynyl Arylketones: Regioselective Synthesis of Functionalized Cinnolines
Yao, Biao,Miao, Tao,Wei, Wei,Li, Pinhua,Wang, Lei
supporting information, p. 9291 - 9295 (2019/12/30)
A novel copper-catalyzed cascade reaction of arylsulfonylhydrazones derived from ortho-alkynyl arylketones was accomplished. This reaction provides concise access to diversified cinnolines in good yields. The mechanistic investigations have disclosed involvement of the key alkynyl amination, 1,4-aryl migration, desulfonylation, and diazo radical cyclization cascade in the transformation.
Triflic acid-Mediated Expedient Synthesis of Benzo[a]fluorenes and Fluorescent Benzo[a]fluorenones
Mandal, Mou,Balamurugan, Rengarajan
supporting information, p. 1453 - 1465 (2018/02/26)
Fluorene-based polyaromatic hydrocarbons are renowned compounds for materials applications. Herein, a straightforward route via in situ acetal formation has been presented to access benzo[a]fluorenes by a triflic acid promoted cationic cycloisomerization
Selective construction of polycyclic spirooxindoles: Via a Cu(OTf)2/HOTf-catalyzed domino reaction of o -arylalkynylacetophenones and 3-phenacylideneoxindoles
Yang, Ren-Yin,Sun, Jing,Sun, Qiu,Yan, Chao-Guo
supporting information, p. 6353 - 6357 (2017/08/10)
Under the combined catalysis of Cu(OTf)2/HOTf, the domino annulation reaction of o-arylalkynyl acetophenones with 3-phenacylideneoxindoles in refluxing acetonitrile selectively afforded functionalized spiro[indoline-3,7′-tetrapheno[7,6-bc]furan
Asymmetric Hydrogenation of In Situ Generated Isochromenylium Intermediates by Copper/Ruthenium Tandem Catalysis
Miao, Tingting,Tian, Zi-You,He, Yan-Mei,Chen, Fei,Chen, Ya,Yu, Zhi-Xiang,Fan, Qing-Hua
supporting information, p. 4135 - 4139 (2017/04/03)
The first asymmetric hydrogenation of in situ generated isochromenylium derivatives is enabled by tandem catalysis with a binary system consisting of Cu(OTf)2 and a chiral cationic ruthenium–diamine complex. A range of chiral 1H-isochromenes were obtained in high yields with good to excellent enantioselectivity. These chiral 1H-isochromenes could be easily transformed into isochromanes, which represent an important structural motif in natural products and biologically active compounds. The chiral induction was rationalized by density functional theory calculations.
Catalytic Sulfur-Enabled Dehydrobicyclization of 1,6-Enynes toward Arylated Indeno[1,2-c]thiophenes
Wu, Ya-Nan,Fu, Rong,Wang, Nan-Nan,Hao, Wen-Juan,Li, Guigen,Tu, Shu-Jiang,Jiang, Bo
, p. 4762 - 4770 (2016/07/06)
A new copper-catalyzed sulfur-enabled dehydrobicyclization of 1,6-enynes using potassium sulfide as a sulfurating reagent has been established, providing a straightforward access toward arylated indeno[1,2-c]thiophenes with moderate to good yields. This sulfur incorporation pathway involves Michael addition, 5-exo-dig/5-endo-trig bicyclization and dehydrogenation sequence, resulting in continuous multiple bond-forming events including C-S and C-C bonds to rapidly construct functional organic molecules.
Synthesis of chrysene derivatives via copper-catalyzed one-pot dimerization of 2-alkynyl-1-acetylbenzenes
Guo, Biao,Zheng, Liyao,Yang, Lichen,Hua, Ruimao
, p. 4352 - 4357 (2014/06/09)
An efficient route for highly substituted chrysene derivatives via operationally simple copper-catalyzed one-pot dimerization of 2-alkynyl-1-acetylbenzenes is described.
Synthesis of naphthalene derivatives from ortho -alkynylacetophenone derivatives via tandem in situ incorporation of acetal and intramolecular heteroalkyne metathesis/annulation
Manojveer, Seetharaman,Balamurugan, Rengarajan
supporting information, p. 1712 - 1715 (2014/04/17)
An interesting domino reaction for the synthesis of substituted naphthyl ketones has been developed using readily accessible starting materials. This domino reaction proceeds via in situ incorporation of an acetal followed by intramolecular heteroalkyne metathesis/annulation in an ortho- alkynylacetophenone derivative. A deuterium incorporation experiment has been carried out to understand the mechanism.
