5272-36-6Relevant articles and documents
Synthesis of cyclic polyelectrolyte via direct copper(I)-catalyzed click cyclization
Chen, Fenggui,Liu, Guangming,Zhang, Guangzhao
, p. 831 - 835 (2012)
Well-defined cyclic poly(acrylic acid) (PAA) has been successfully prepared based on the direct click cyclization. The linear poly(tert-butyl acrylate) (PtBA) with azide and TMS-protected alkyne group forms cyclic chain directly by the copper(I)-catalyzed click cyclization without any deprotection steps. Cyclic PAA is synthesized by the hydrolysis of cyclic PtBA. The present synthetic strategy provides a simple and efficient method to synthesize cyclic polyelectrolyte and can be applied to other polymer systems. Copyright
Silver-catalyzed heterocyclization: First total synthesis of the naturally occurring cis 2-hexadecyl-3-hydroxy-4-methylene butyrolactone
Dalla,Pale
, p. 3525 - 3528 (1994)
The title compound was obtained in 4 steps with an overall yield of 64% with the silver-catalyzed cyclization of the corresponding substituted β-hydroxy-γ-acetylenic acid as the key step.
Silicon-directed decarbonylation of trimethylsilyl β,γ-enals by photolysis
Hwu,Furth
, p. 8834 - 8841 (1989)
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Development of a Radical Silylzincation of (Het)Aryl-Substituted Alkynes and Computational Insights into the Origin of the trans-Stereoselectivity
Romain, Elise,de la Vega-Hernández, Karen,Guégan, Frédéric,Sanz García, Juan,Fopp, Carolin,Chemla, Fabrice,Ferreira, Franck,Gerard, Hélène,Jackowski, Olivier,Halbert, Stéphanie,Oestreich, Martin,Perez-Luna, Alejandro
supporting information, p. 2634 - 2647 (2021/03/30)
Aryl- and hetaryl-substituted acetylenes undergo regio- and stereoselective silylzincation by reaction with [(Me3Si)3Si]2Zn in the presence of Et2Zn (10–110 mol%) as additive. The distinctive feature of this addition across the C?C triple bond is its trans stereoselectivity. The radical nature of the silylzincation process is supported by diagnostic experiments and DFT calculations, which also corroborate the role played by steric effects to obtain that stereoselectivity. The procedure can be combined in one-pot with the copper(I)-mediated electrophilic substitution of the C(sp2)?Zn bond, with retention of the double bond geometry. This makes it valuable for the synthesis of stereodefined di- and trisubstituted vinylsilanes. (Figure presented.).
Low-valent dialkoxytitanium(ii): a useful tool for the synthesis of functionalized seven-membered ring compounds
Bodinier, Florent,Sanogo, Youssouf,Ardisson, Janick,Lannou, Marie-Isabelle,Sorin, Geoffroy
supporting information, p. 3603 - 3606 (2021/04/14)
Herein, we describe unprecedented access to all-carbon or heterocyclic seven-membered ring frameworks from 1,8-ene-ynes promoted by inexpensive low-valent titanium(ii) species, readily available from Ti(OiPr)4and Grignard reagent. A broad range of cycloheptane, azepane or oxepane derivatives has been obtained (19 examples) with moderate to good yields and an excellent selectivity (up to 95/5 d.r.).
Copper-Catalyzed Modular Access to N-Fused Polycyclic Indoles and 5-Aroyl-pyrrol-2-ones via Intramolecular N—H/C—H Annulation with Alkynes: Scope and Mechanism Probes
Liu, Yan-Hua,Song, Hong,Zhang, Chi,Liu, Yue-Jin,Shi, Bing-Feng
supporting information, p. 1545 - 1552 (2020/09/09)
Copper-catalyzed intramolecular N—H/C—H annulation with alkynes has been developed. A variety of densely functionalized heterocycles, such as pyrrolo[1,2-a]indoles, indolo[1,2-c]quinazolin-2-ones, oxazolo[3,4-a]indoles, and imidazo[1,5-a]indoles, were synthesized in an atom- and step-economical manner, owing to the high modularized feature of aniline moiety, the linker moiety, as well as the alkyne moiety. By simply changing the oxidant from di-tert-butyl peroxide (DTBP) to 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO), the reaction could readily be transformed to the aminooxygenation pathway, which grabs one oxygen atom from the TEMPO to generate 5-aroyl-pyrrol-2-ones. Mechanistic experiments indicate that vinyl radical is involved in this reaction and an amidyl-radical-initiated radical cascade might be responsible for this transformation.