18773-54-1Relevant academic research and scientific papers
Ru3(CO)12-catalyzed reaction of 1,6-diynes, carbon monoxide, and water via the reductive coupling of carbon monoxide
Crudden, Cathleen M.,Maekawa, Yuuki,Clarke, Joshua J.,Ida, Tomohide,Fukumoto, Yoshiya,Chatani, Naoto,Murai, Shinji
, p. 8747 - 8751 (2020)
We report the ruthenium-catalyzed cyclization of 1,6-diynes with two molecules of carbon monoxide and water to give a variety of catechols. This reaction likely proceeds through the intermediacy of the water-gas shift reaction to generate an yne- diol-typ
A New Approach for the Synthesis of Highly Substituted Aromatic Rings: The Alkyne-Mediated Approach
Parsons, Philip J.,Jones, Daniel R.,Padgham, Alex C.,Allen, Lewis A. T.,Penkett, Clive S.,Green, Robert A.,White, Andrew J. P.
, p. 3981 - 3984 (2016)
Pentasubstituted aromatic rings serve as templates for drug design and can be conveniently prepared by the thermolysis of suitably substituted alkynes under microwave conditions. Rings in the microwave! Pentasubstituted aromatic rings serve as templates for drug design and can be conveniently prepared by the thermolysis of suitably substituted alkynes under microwave conditions.
A Rh-Catalyzed Cycloisomerization/Diels-Alder Cascade Reaction of 1,5-Bisallenes for the Synthesis of Polycyclic Heterocycles
Artigas, Albert,Vila, Jordi,Lledó, Agustí,Solà, Miquel,Pla-Quintana, Anna,Roglans, Anna
, p. 6608 - 6613 (2019)
A novel methodology to transform bisallenes into a variety of polycyclic derivatives employing rhodium(I) catalysis has been developed. This transformation encompasses an intramolecular Rh-catalyzed cycloisomerization of bisallenes 1 to deliver a reactive
Imino Diels-Alder/transition metal catalyzed reactions to synthesise fused ring heterocycles
Alter, Alexander,Pask, Christopher M.,Sridharan, Visuvanathar,Taylor, Connor J.
, (2020)
Imino Diels-Alder reactions were tactically combined with various transition metal catalysed [2 + 2], [3 + 2] and [4 + 2] cycloaddition reactions to form novel syntheses for biologically relevant fused-ring heterocycles with molecular complexity in good y
Epoxyanthracene Derivatives and Dicarbonylation on Benzene Ring via Hexadehydro-Diels-Alder (HDDA) Derived Benzynes with Oxazoles
Yang, Feihu,Zheng, Xiaojie,Lei, Yu,Hu, Qiong,Zhu, Wenjing,Hu, Yimin
supporting information, p. 1125 - 1133 (2021/11/22)
A capture reaction of hexadehydro-Diels-Alder (HDDA) derived benzyne with various substituted oxazoles is reported. With methyl, hydrogen, or phenyl as the substituent at 2-position of oxazole, tetraynes afforded epoxyanthracene derivatives or underwent dicarbonylation on benzene ring. The reaction does not require any catalyst or additive. The mechanism behind the reaction was investigated. The obtained polycyclic product structure has potential application value in optoelectronic materials. The availability of dicarbonylated arene implies the uniqueness of HDDA benzyne reaction compared with traditional benzyne.
A Rh(I)-Catalyzed Cascade Cyclization of 1,5-Bisallenes and Alkynes for the Formation of cis-3,4-Arylvinyl Pyrrolidines and Cyclopentanes
Vila, Jordi,Vinardell, Roger,Solà, Miquel,Pla-Quintana, Anna,Roglans, Anna
supporting information, p. 206 - 217 (2021/11/17)
The cascade cyclization reactions of 1,5-bisallenes grant access to a great variety of products by precisely tuning the catalyst system and/or the reagents involved. Herein, we present our findings that 1,5-bisallenes react with two molecules of dimethyl acetylenedicarboxylate to afford, in a completely diastereoselective manner, cis-3,4-arylvinyl pyrrolidines and cyclopentanes. DFT calculations have been used to postulate a mechanism for the developed reaction which encompasses a [2+2+2] cycloaddition reaction of the two alkynes and the external double bond of one allene, followed by a cycloisomerization involving the internal double bond of the second allene. (Figure presented.).
Fully Substituted Conjugate Benzofuran Core: Multiyne Cascade Coupling and Oxidation of Cyclopropenone
Yao, Liangliang,Hu, Qiong,Bao, Li,Zhu, Wenjing,Hu, Yimin
supporting information, p. 4971 - 4975 (2021/06/30)
An unprecedented C═C double bond cleavage of cyclopropenone and dioxygen activation by multiyne cascade coupling has been developed. This chemistry provides a novel, simple, and efficient approach to synthesize fully substituted conjugate benzofuran derivatives from simple substrates under mild conditions. The density functional theory (DFT) calculations reveal that the unique homolytic cleavages of cyclopropenone and molecular oxygen are crucial to the success of this reaction.
Synthesis of Fused Dihydroazepine Derivatives of Fullerenes by a Rh-Catalyzed Cascade Process
Artigas, Albert,Castanyer, Cristina,Lledó, Agustí,Pla-Quintana, Anna,Roglans, Anna,Roig, Nil,Solà, Miquel
supporting information, p. 3835 - 3844 (2021/07/02)
A synthetic methodology is reported that functionalizes C60 and C70 fullerenes with dihydroazepine rings by a cascade reaction encompassing a rhodium-catalyzed cycloisomerization of 1,5-bisallenes and a [4+2] cycloaddition. This tran
Enantioselective Rh(II)-Catalyzed Desymmetric Cycloisomerization of Diynes: Constructing Furan-Fused Dihydropiperidines with an Alkyne-Substituted Aza-Quaternary Stereocenter
Cao, Tongxiang,Chen, Kai,Lu, Jiajun,Ma, Jun,Wu, Rui,Zhu, Shifa
supporting information, p. 14916 - 14925 (2021/09/18)
Described herein is an enantioselective dirhodium(II)-catalyzed cycloisomerization of diynes achieved by the strategy of desymmetrization, which not only represents a new cycloisomerization reaction of diynes but also constitutes the first Rh(II)-catalyzed asymmetric intramolecular cycloisomerization of 1,6-diynes. This protocol provides a range of valuable furan-fused dihydropiperidine derivatives with an enantiomerically enriched alkynyl-substituted aza-quaternary stereocenter in high efficiency, complete atom economy, and excellent enantioselectivity (up to 98% ee). Besides, the highly functionalized products could be easily transformed into various synthetically useful building blocks and conjugated with a series of pharmaceutical molecules. The mechanism involving a concerted [3+2] cycloaddition/[1,2]-H shift of the Rh(II) carbenoid intermediate was elucidated by DFT calculations and mechanistic studies. More importantly, the first single crystal of alkyne-dirhodium(II) was obtained to show that a η2-coordinating activation of alkynal by dirhodium(II) was involved. Weak hydrogen bondings between the carboxylate ligands and alkynal were found, which probably made the well-defined paddlewheel-like dirhodium(II) distinctive from other metal complexes in catalyzing this transformation. Furthermore, the origin of the enantioselectivity was elucidated by a Rh2(R-PTAD)4-alkyne complex and additional calculational studies.
Access to Benzoxazepines and Fully Substituted Indoles via HDDA Coupling
Zheng, Xiaojie,Liu, Baohua,Yang, Feihu,Hu, Qiong,Yao, Liangliang,Hu, Yimin
supporting information, p. 956 - 959 (2020/02/15)
The HDDA-derived benzyne intermediate was captured by oxazolines based on the addition reaction of benzyne to the Ca?N double bond. Benzoxazepine derivatives, fused benzoxazepine derivatives, and fully substituted indoles are synthesized in one step. The reaction does not require any catalyst or additives. Possible reaction mechanisms are presented.
