261713-83-1Relevant articles and documents
An on-surface Diels–Alder reaction
Albrecht, Florian,Castro-Esteban, Jesús,Fatayer, Shadi,Gross, Leo,Pérez, Dolores,Pe?a, Diego
supporting information, p. 26346 - 26350 (2021/11/13)
The Diels–Alder reaction is one of the most popular reactions in organic chemistry. However, its use in the field of on-surface synthesis is hampered by the spatial restrictions of this cycloaddition reaction. Herein we selected a cyclic strained triyne t
Selective Synthesis of Phenanthrenes and Dihydrophenanthrenes via Gold-Catalyzed Cycloisomerization of Biphenyl Embedded Trienynes
Milián, Ana,Garciá-Garciá, Patricia,Pérez-Redondo, Adrián,Sanz, Roberto,Vaquero, Juan J.,Fernández-Rodríguez, Manuel A.
supporting information, p. 8464 - 8469 (2020/11/02)
Readily available o′-alkenyl-o-alkynylbiaryls, a particular type of 1,7-enynes, undergo a selective cycloisomerization reaction in the presence of a gold(I) catalyst to give interesting phenanthrene and dihydrophenanthrene derivatives in high yields. The solvent used provokes a switch in the evolution of the gold intermediate and plays a key role in the reaction outcome.
Syntheses of substituted benzosiloles and siloles by diisobutylaluminium hydride-promoted cyclization of 1-silyl-2-(2-silylethynyl)benzenes and 1,4-disilylalk-3-en-1-ynes
Kinoshita, Hidenori,Fukumoto, Hiroki,Ueda, Akihiro,Miura, Katsukiyo
, p. 1632 - 1645 (2018/02/19)
An efficient method for preparing substituted benzosiloles and unsymmetrically substituted siloles by intramolecular C-Si bond formation has been developed. The reaction of 1-methoxysilyl-2-[2-(trimethylsilyl)ethynyl]benzenes with 1.5 equiv of diisobutylaluminium hydride (DIBAL-H) gave benzosiloles in good to high yields. Similarly 4-methoxysilyl-1-silylalk-3-en-1-ynes were cyclized to multisubstituted siloles. Mechanistic study of this transformation uncovered that the methoxysilyl group was initially converted into the corresponding hydrosilyl group by the action of DIBAL-H, and that the resultant hydrosilanes underwent the DIBAL-H-promoted cyclization to benzosiloles. When 1-hydrosilyl-2-[2-(trimethylsilyl)ethynyl]benzenes were used as substrates, a substoichiometric amount of DIBAL-H was enough for the cyclization. The DIBAL-H-promoted transformation could be applied to regio-defined synthesis of unsymmetrically substituted siloles from 4-hydrosilyl-1-silylalk-3-en-1-ynes. This pre-installation approach provides a straightforward access to multisubstituted siloles with complete regioselection.