80907-80-8Relevant articles and documents
Iron-Catalyzed Tertiary Alkylation of Terminal Alkynes with 1,3-Diesters via a Functionalized Alkyl Radical
Tian, Ming-Qing,Shen, Zhen-Yao,Zhao, Xuefei,Walsh, Patrick J.,Hu, Xu-Hong
supporting information, p. 9706 - 9711 (2021/03/19)
Direct oxidative C(sp)?H/C(sp3)?H cross-coupling offers an ideal and environmentally benign protocol for C(sp)?C(sp3) bond formations. As such, reactivity and site-selectivity with respect to C(sp3)?H bond cleavage have remained a persistent challenge. Herein is reported a simple method for iron-catalyzed/silver-mediated tertiary alkylation of terminal alkynes with readily available and versatile 1,3-dicarbonyl compounds. The reaction is suitable for an array of substrates and proceeds in a highly selective manner even employing alkanes containing other tertiary, benzylic, and C(sp3)?H bonds alpha to heteroatoms. Elaboration of the products enables the synthesis of a series of versatile building blocks. Control experiments implicate the in situ generation of a tertiary carbon-centered radical species.
DBU-Mediated Synthesis of Aryl Acetylenes or 1-Bromoethynylarenes from Aldehydes
Thummala, Yadagiri,Karunakar, Galla V.,Doddi, Venkata Ramana
supporting information, p. 611 - 616 (2019/01/04)
Two well known synthetic organic reactions Ramirez olefination and Corey-fuchs reactions are integrated in one-pot sequential manner for the synthesis of arylacetylenes and 1,3-enynes starting directly from commercially available aldehydes. The bicyclic amidine 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) along with additive NaOH not only exclusively afforded the terminal alkynes directly from the aldehydes, but also enhanced the reaction rate. The dynamic nature of DBU also facilitated the isolation of 1-bromoalkynes intermediate products. Selection of additive from NaOH and H2O served as a switch for the synthesis of terminal alkyne and 1-bromoalkynes, respectively. (Figure presented.).
Contiguous Quaternary Centers from a AuI-Catalyzed Nazarov Cyclization
Congmon, Jonathan,Tius, Marcus A.
supporting information, p. 2926 - 2930 (2018/06/27)
The cationic AuI-catalyzed cyclization of highly substituted enynes has been shown to provide cyclopentenones with up to two contiguous, all-carbon atom quaternary centers in a diastereospecific process. In the more challenging examples in whic
One-Pot Relay Gold(I) and Br?nsted Acid Catalysis: Cyclopenta[b]annulation of Indoles via Hydroamination/Nazarov-Type Cyclization Cascade of Enynols
Dhiman, Seema,Ramasastry
supporting information, p. 5116 - 5119 (2015/11/03)
An expedient relay gold(I) and Br?nsted acid catalyzed hydroamination/Nazarov cyclization of 1-(2-aminophenyl)pent-4-en-2-ynols for the synthesis of various polyfunctionalized cyclopenta[b]indoles is described. The synthetic utility of this method has bee
Regioselective hydrations of 1-aryl-3-en-1-ynes using gold and platinum catalysts: Selective production of 2-en-1-ones and 3-en-1-ones
Mokar, Bhanudas Dattatray,Liu, Rai-Shung
supporting information, p. 8966 - 8969 (2014/08/05)
Regiocontrolled hydrations of 1-aryl-3-en-1-ynes have been accomplished with IPrAuOTf and PtCl2/CO to yield 3-en-1-ones and 2-en-1-ones efficiently; our experimental data indicates that the sizes of catalysts play an important role. This journa
Gold-catalyzed synthesis of substituted 2-aminofurans via formal [4+1]-cycloadditions on 3-en-1-ynamides
Dateer, Ramesh B.,Pati, Kamalkishore,Liu, Rai-Shung
supporting information; experimental part, p. 7200 - 7202 (2012/08/07)
Gold-catalyzed formal [4+1]-cycloadditions between 3-en-1-ynamides 1 and 8-methylquinoline oxide are reported. The success of this reaction relies on a hypothetic oxa-Nazarov cyclization on gold-stabilized allylic cations. Preliminary results on a new 1,2-difunctionalization of 3-en-1-ynamide are also reported.
Catalytic dicyanative [4 + 2] cycloaddition triggered by cyanopalladation using ene-enynes and cyclic enynes with methyl acrylate
Arai, Shigeru,Koike, Yuka,Hada, Hirohiko,Nishida, Atsushi
supporting information; experimental part, p. 7573 - 7579 (2011/02/25)
Palladium-catalyzed dicyanative [4 + 2] cycloaddition using various ene-enynes was investigated. The key species in this process is a cyanoallene intermediate that is obtained by the cyanopalladation of conjugated enynes followed by 5-exo-cyclization. To
Diazoethenes: Their Attempted Synthesis from Aldehydes and Aromatic Ketones by Way of the Horner-Emmons Modification of the Wittig Reaction. A Facile Synthesis of Alkynes
Gilbert, J. C.,Weerasooriya, U.
, p. 1837 - 1845 (2007/10/02)
The base-promoted reaction of dimethyl (diazomethyl)phosphonate (8) with aldehydes and aryl ketones at low temperatures has been investigated.Alkynes, in modest to excellent yields, are the predominant products of these reactions, a result consistent with the intervention of diazoethenes (3).The latter appear to be unstable toward unimolecular decomposition at -78 deg C and yield nitrogen and alkylidenecarbenes (1).
