- Photocatalyzed Intramolecular [2+2] Cycloaddition of N-Alkyl-N-(2-(1-arylvinyl)aryl)cinnamamides
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N-Alkyl-N-(2-(1-arylvinyl)aryl)cinnamamides are converted into natural product inspired scaffolds via iridium photocatalyzed intramolecular [2+2] photocycloaddition. The protocol has a broad substrate scope, whilst operating under mild reaction conditions. Tethering four components forming a trisubstituted cyclobutane core builds rapidly high molecular complexity. Our approach allows the design and synthesis of a variety of tetrahydrocyclobuta[c]quinolin-3(1H)-ones, in yields ranging between 20–99 %, and with excellent regio- and diastereoselectivity. Moreover, it was demonstrated that the intramolecular [2+2]-cycloaddition of 1,7-enynes—after fragmentation of the cyclobutane ring—leads to enyne-metathesis-like products.
- de Souza, Wanderson C.,Matsuo, Bianca T.,Matos, Priscilla M.,Correia, José Tiago M.,Santos, Marilia S.,K?nig, Burkhard,Paix?o, Marcio W.
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supporting information
p. 3722 - 3728
(2021/02/03)
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- Palladium(ii)-catalyzed vinylic geminal double C-H activation and alkyne annulation reaction: Synthesis of pentafulvenes
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The first transition-metal-catalyzed vinylic geminal double C(sp2)-H activation and di-substituted alkyne annulation reaction is reported. This palladium(ii)-catalyzed, amide directed reaction of vinylic compounds with di-substituted alkynes offers an efficient synthetic path to pentafulvenes, which are very important compounds because of their bioactivity and interesting optical properties. A FeCl3-mediated transformation of pentafulvenes to fluorescent cyclopenta[b]quinolines is also developed.
- Phukon, Jyotshna,Gogoi, Sanjib
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supporting information
p. 1133 - 1136
(2020/02/04)
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- Mn(III)-Mediated Regioselective 6-endo-trig Radical Cyclization of o-Vinylaryl Isocyanides to Access 2-Functionalized Quinolines
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A Mn(III)-mediated radical cyclization reaction of o-vinylaryl isocyanides and arylboronic acids or diphenylphosphine oxides to access various 2-functionalized quinolines under mild conditions was developed. With the introduction of radical stabilizing substituents (e. g. aryl and methyl group) on vinyl group, this reaction provides a regiospecific 6-endo-trig radical cyclization of o-vinylaryl isocyanides, giving a number of structurally unique and biologically potential 2-functionalized quinoline derivatives.
- Liu, Yan,Li, Shi-Jun,Chen, Xiao-Lan,Fan, Lu-Lu,Li, Xiao-Yun,Zhu, Shan-Shan,Qu, Ling-Bo,Yu, Bing
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supporting information
p. 688 - 694
(2020/01/02)
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- Palladium-Catalyzed Phosphoryl-Carbamoylation of Alkenes: Construction of Nonbenzylic C(sp3)?P(O)R2 Bonds via C(sp3)?Pd(II)?P(O)R2 Reductive Elimination
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We report the first example of palladium-catalyzed phosphoryl-carbamoylation of alkene-tethered carbamoyl chlorides with P(O)H compounds. Both H-phosphinates and secondary phosphine oxides are compatible with this reaction. DPE-Phos was used as ligand to facilitate nonbenzylic C(sp3)?P bonds formations via C(sp3)?Pd(II)?P reductive elimination. By using this protocol, a range of phosphorylated oxindoles and lactams were obtained in moderate to good yields. (Figure presented.).
- Chen, Chen,Sun, Wan,Yan, Yan,Yang, Fang,Wang, Yuebo,Zhu, Yan-Ping,Liu, Liying,Zhu, Bolin
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supporting information
p. 2970 - 2975
(2020/07/06)
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- Palladium-Catalyzed/Copper-Mediated Desulfurization and Aryl- ation of Quinoline-2-(1 H)-thione for Rapid Access to Quinoline Derivatives
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An efficient method for carbon-carbon bond formation is described. The process employs the palladium-catalyzed and copper-mediated cross-coupling of quinoline-2-(1 H)-thiones with arylboronic acids or alkynes through C-S bond cleavage without an inert atm
- Guo, Fu-Hu,Lu, Hai-Long,Quan, Zheng-Jun,Wang, Tong-Lin,Wang, Xi-Cun
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supporting information
p. 893 - 900
(2020/03/13)
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- Chemo- And Regioselective Magnesium-Catalyzed ortho-Alkenylation of Anilines
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A simple and efficient catalytic system for a chemo- and regioselective ortho-alkenylation of anilines is presented. The new magnesium-catalyzed reaction allows the use of a wide range of alkynes and anilines with different electronic and steric propertie
- Chatupheeraphat, Adisak,Rueping, Magnus,Magre, Marc
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supporting information
p. 9153 - 9157
(2019/11/14)
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- Cleavage of C-C Bonds for the Synthesis of C2-Substituted Quinolines and Indoles by Catalyst-Controlled Tandem Annulation of 2-Vinylanilines and Alkynoates
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The strategy for the synthesis of C2-substituted indoles and quinolines from 2-vinylanilines and alkynoates through C-C bond cleavage is developed. With these general methods, 2-substituted indoles and quinolines can be accessed via tandem Michael addition and cyclization with no requirement of oxidant. This strategy not only provides a method for the synthesis C2-substituted indoles in good yields through the simultaneous cleavage of C=C and C=C bonds under metal-free conditions but also provides a simple method for the generation of the C2-substituted quinolines in moderate yields via Pd-catalyzed C=C bond cleavage.
- Ni, Jixiang,Jiang, Yong,An, Zhenyu,Yan, Rulong
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supporting information
p. 1534 - 1537
(2018/03/23)
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- Base-catalyzed thio-lactamization of 2-(1-arylvinyl)anilines with CS2 for the synthesis of quinoline-2-thiones
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Here we show that the base-catalyzed thio-lactamization of 2-(1-arylvinyl)anilines with CS2 is a powerful methodology to synthesize quinoline-2-thiones. This thio-lactamization uses inexpensive and versatile 2-(1-arylvinyl)anilines, which are easily available from the reaction of amines and alkynes. Compared to the known strategy in the literature, this method features the advantages like a short synthesis step and easily available starting materials.
- Wang, Tong-Lin,Liu, Xiao-Jun,Huo, Cong-De,Wang, Xi-Cun,Quan, Zheng-Jun
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supporting information
p. 499 - 502
(2018/01/19)
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- Base-controlled chemoselectivity reaction of vinylanilines with isothiocyanates for synthesis of quinolino-2-thione and 2-aminoquinoline derivatives
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Here, we report a base-controlled chemo-selective reaction of vinylanilines with alkyl/aryl isothiocyanates to afford quinolino-2-thione and 2-aminoquinoline derivatives. The quinolino-2-thiones could be obtained in high yields in the presence of Et3N. Particularly interesting is that the reaction could produce the 2-aminoquinolines in the presence of K3PO4 with high selectivity.
- Zhang, Xi,Wang, Tong-Lin,Huo, Cong-De,Wang, Xi-Cun,Quan, Zheng-Jun
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supporting information
p. 3114 - 3117
(2018/03/28)
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- Copper-mediated intramolecular aza-Wacker-type cyclization of 2-alkenylanilines toward 3-aryl indoles
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A copper-mediated intramolecular aza-Wacker-type cyclization was developed for the direct and efficient synthesis of 3-aryl indoles using 2-alkenylanilines in moderate to good yields with good functional group compatibility. This strategy shows the high efficiency, operational simplicity as well as broad substrate scope.
- Yang, Rui,Yu, Jin-Tao,Sun, Song,Zheng, Qingheng,Cheng, Jiang
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supporting information
p. 445 - 448
(2017/01/11)
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- Carbon annulation of ortho-vinylanilines with dimethyl sulfoxide to access 4-aryl quinolines
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A palladium-catalyzed annulation of ortho-vinylanilines with dimethyl sulfoxide was developed to access 4-aryl quinolines in moderate to good yields. Activated by 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABSO), DMSO served as a “=CH-” fragment in this transformation. It represents a facile pathway leading to 4-aryl quinolines.
- Yuan, Jin,Yu, Jin-Tao,Jiang, Yan,Cheng, Jiang
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supporting information
p. 1334 - 1337
(2017/02/15)
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- Tert -Butyl nitrite (TBN) as the N atom source for the synthesis of substituted cinnolines with 2-vinylanilines and a relevant mechanism was studied
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A green method to synthesize cinnolines by 6π electrocyclic reaction with alkenyl amines and TBN has been developed. TBN plays a dual role both as a nitrogen atom source and an oxidant in this procedure. Relevant mechanism experiments reveal that the reaction proceeds through electrocyclic reaction and with diazo hydroxide as a key intermediate.
- Pang, Xiaobo,Zhao, Lianbiao,Zhou, Dagang,He, Ping Yong,An, Zhenyu,Ni, Ji Xiang,Yan, Rulong
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supporting information
p. 6318 - 6322
(2017/08/10)
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- Palladium-Catalyzed Domino Alkenylation/Amination/Pyridination Reactions of 2-Vinylanilines with Alkynes: Access to Cyclopentaquinolines
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A novel domino oxidative annulation of 2-vinylanilines with internal alkynes was developed to constitute a rare class of cyclopentaquinoline derivatives. This transformation encompasses four σ bonds formation, one quaternary carbon center construction, and pyridination steps in one pot under identical conditions, which fascinatingly increases the molecular complexity from easily available starting materials.
- Li, Dejun,Zeng, Fanlong
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supporting information
p. 6498 - 6501
(2017/12/26)
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- Copper-catalyzed tandem aerobic oxidative cyclization for the ynthesis of polysubstituted quinolines via C(sp3)/C(sp2)-H bond functionalization
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One-pot Cu-catalyzed tandem aerobic oxidative cyclization for the synthesis of quinolines from 2-vinylanilines/ 2-arylanilines and 2-methylquinolines via C(sp3)-H/C(sp2)- H bond functionalization has been developed. Dioxygen as an ideal oxidant has been employed for this transformation. The substrates bearing various functional groups perform well in this process and generate the desired products in moderate to good yields.
- Pang, Xiaobo,Wu, Mingzhong,Ni, Jixiang,Zhang, Fuming,Lan, Jingfeng,Chen, Baohua,Yan, Rulong
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p. 10110 - 10120
(2018/05/31)
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- Addition of alkynes to a gallium bis-amido complex: Imitation of transition-metal-based catalytic systems
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Acetylene, phenylacetylene, and alkylbutynoates add reversibly to (dpp-bian)Ga-Ga(dpp-bian) (dpp-bian=1,2-bis[(2,6-diisopropylphenyl)-imino] acenaphthene) to give addition products [dpp-bian(R1C=CR 2)]Ga-Ga[(R2C=CR1/
- Fedushkin, Igor L.,Nikipelov, Alexander S.,Morozov, Alexander G.,Skatova, Alexandra A.,Cherkasov, Anton V.,Abakumov, Gleb A.
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supporting information; experimental part
p. 255 - 266
(2012/02/16)
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