108357-95-5Relevant articles and documents
Practical synthesis of α,β-Alkynyl ketones by oxidative alkynylation of aldehydes with hypervalent alkynyliodine reagents
Tsuzuki, Saori,Sakamoto, Ryu,Maruoka, Keiji
, p. 633 - 636 (2020)
A practical, metal-free carbonyl C(sp2)H oxidative alkynylation of aldehydes with hypervalent alkynyliodine reagents without the use of any catalysts is described for the synthesis of various α,β-alkynyl ketones. Here, two different methods have been developed where limiting reagents or substrates can be switched, and adopted according to the valuableness of aldehyde substrates or hypervalent alkynyliodine reagents. These reactions proceed with a broad substrate scope and high functional-group compatibility.
Coupling and carbonylation of iodoaromatics and terminal alkynes or alkynols catalyzed by a dimeric palladium hydroxide
Delaude,Masdeu,Alper
, p. 1149 - 1151 (1994)
The palladium(II) complex [(Ph3P)Pd(Ph)(μ-OH)]2 is an effective catalyst for the coupling aud carbonylation of alkynes and iodoarenes to give acetylenic ketones in 63-94% yields. Acetylenic hydroxy ketones were formed using secondary or tertiary alkynols as reactants.
Decatungstate as Direct Hydrogen Atom Transfer Photocatalyst for SOMOphilic Alkynylation
Capaldo, Luca,Ravelli, Davide
, p. 2243 - 2247 (2021/04/05)
A versatile approach for the alkynylation of a variety of aliphatic hydrogen donors, including alkanes, is reported. We used tetrabutylammonium decatungstate as photocatalyst to generate organoradicals from C-H/Si-H bonds via hydrogen atom transfer. The l
α- and γ-Regiocontrol and Enantiospecificity in the Copper-Catalyzed Substitution Reaction of Propargylic Phosphates with Grignard Reagents
Kobayashi, Yuichi,Takashima, Yuji,Motoyama, Yuuya,Isogawa, Yukari,Katagiri, Kyosuke,Tsuboi, Atsuki,Ogawa, Narihito
, p. 3779 - 3785 (2021/02/03)
The regioselectivity (r.s.) and enantiospecificity (e.s.) of the substitution reactions of secondary propargylic alcohol derivatives using reagents derived from ArMgBr and Cu salts were studied. First, the picolinate, 3-methylpicolinate, and diethylphosph
Asymmetric transfer hydrogenation of unsaturated ketones; factors influencing 1,4- vs 1,2- regio- and enantioselectivity, and alkene vs alkyne directing effects
Hall, Thomas H.,Adams, Hannah,Vyas, Vijyesh K.,Michael Chu,Wills, Martin
, (2020/12/07)
A detailed study has been completed on the asymmetric transfer hydrogenation (ATH) of a series of enones using Ru(II) catalysts. Electron-rich rings adjacent to the C[dbnd]O group reduce the level of C[dbnd]O reduction compared to C[dbnd]C. The ATH reaction can readily discriminate between double and triple bonds adjacent to ketones, reducing the double bond but leaving a triple bond intact in the major product.
General Synthesis of α-Alkyl Ynones from Morpholine Amides and 1-Copper(I) Alkynes Promoted by Triflic Anhydride
Weng, Yunxiang,Min, Lin,Zeng, Xiaobao,Shan, Lidong,Wang, Xinyan,Hu, Yuefei
supporting information, p. 8296 - 8301 (2020/11/03)
The first general method for the synthesis of α-alkyl ynones was developed based on the strategy of electrophilic activation of amides. Its distinctive advantages are attributed to the use of air-stable "bare"1-copper(I) alkyne as a mild nucleophile witho
Visible light-induced co- or cu-catalyzed selenosulfonylation of alkynes: Synthesis of β-(seleno)vinyl sulfones
Ji, Shun-Jun,Wang, Shun-Yi,Xu, Pei,Zhang, Rong
, (2019/10/08)
A visible light-induced Co- or Cu-catalyzed selenosulfonylation of alkynes for the synthesis of β-(seleno)vinyl sulfones is demonstrated. This method utilizes a low-cost cobalt salt or metal copper as the catalysts. The reaction goes through a photoinduced free radical addition of selenosulfonates to alkynes for the 1,2-selenosulfonylation of alkynes under mild conditions.
Highly regioselective gold-catalyzed formal hydration of propargylic: Gem -difluorides
Hamel, Jean-Denys,Hayashi, Tatsuru,Cloutier, Mélissa,Savoie, Paul R.,Thibeault, Olivier,Beaudoin, Meggan,Paquin, Jean-Fran?ois
, p. 9830 - 9836 (2017/12/08)
Herein, we report a highly regioselective gold-catalyzed formal hydration of propargylic gem-difluorides. Not only does this transformation provide access to versatile fluorinated building blocks that were difficult or hardly possible to access beforehand, but it also represents a rare case of a highly regioselective gold-catalyzed hydroalkoxylation of internal alkynes and puts forward the utility of the difluoromethylene unit as a directing group in catalysis.
Alkynylation of Csp2 (O)–H Bonds Enabled by Photoredox-Mediated Hydrogen-Atom Transfer
Mukherjee, Satobhisha,Garza-Sanchez, R. Aleyda,Tlahuext-Aca, Adrian,Glorius, Frank
, p. 14723 - 14726 (2017/10/18)
The development of new hydrogen-atom transfer (HAT) strategies within the framework of photoredox catalysis is highly appealing for its power to activate a desired C?H bond in the substrate leading to its selective functionalization. Reported here is the first photoredox-mediated hydrogen-atom transfer method for the efficient synthesis of ynones, ynamides, and ynoates with high regio- and chemoselectivity by direct functionalization of Csp2 (O)?H bonds. The broad synthetic application of this method has been demonstrated by the selective functionalization of C(O)?H bonds within complex molecular scaffolds.
Direct synthesis of pyrazoles from esters using tert-butoxide-assisted C-(C=O) coupling
Kim, Bo Ram,Sung, Gi Hyeon,Ryu, Ki Eun,Lee, Sang-Gyeong,Yoon, Hyo Jae,Shin, Dong-Soo,Yoon, Yong-Jin
supporting information, p. 9201 - 9204 (2015/06/08)
This paper describes the direct synthesis of pyrazoles from esters that comprises two sequential reactions: tert-butoxide-assisted C-C(=O) coupling reaction to yield β-ketonitrile or α,β-alkynone intermediates, and condensation by hydrazine addition. The method reported allows for easy control of the regioselectivity and structure of substituents at N-1, C-3, C-4 and/or C-5 positions.
