18773-54-1Relevant articles and documents
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
First demonstration of helical chirality in 1,4-disubstituted (Z,Z)-1,3-dienes: R3Si-SnR'3-mediated cyclization of 1,6-diynes [11]
Greau, Sandra,Radetich, Branko,Rajanbabu
, p. 8579 - 8580 (2000)
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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.
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.