13829-77-1Relevant articles and documents
An efficient palladium-catalyzed coupling reaction of lithium alkynyltriisopropoxyborates with acid chlorides: A new access to synthesis of conjugated ynones
Oh, Chang Ho,Reddy, V. Raghava
, p. 8545 - 8548 (2004)
An efficient palladium-catalyzed protocol for the synthesis of ynones from lithium alkynyltriisopropoxyborates with acid chlorides under mild neutral conditions.
Ni(0) catalyzed one step synthesis of benzo[b][1,8] naphthyridin-5-ones from silyl-α-ketoalkynes in water
Suárez-Ortiz, Gloria Alejandra,Sharma, Pankaj,Amézquita-Valencia, Manuel,Arellano, Ivonne,Cabrera,Rosas, Noé
, p. 1641 - 1643 (2011)
One-step synthesis of new benzo[b][1,8]naphthyridin-5-ones using a Ni(0) catalytic system in aqueous medium with mild conditions of pressure and temperature is described. It is very interesting to note that Ni(0) catalyst increases the rate of condensation of several α-ketoalkynes with 2-amino-4(1H)-quinolinone obtaining benzo[b][1,8]naphthyridin-5-ones in very high yield. In the absence of catalyst this condensation reaction takes 24 h with a product yield of 10%.
Palladium-Catalyzed Reactions of Acyl Chlorides with (1-Alkynyl)tributylstannanes. A Convenient Synthesis for 1-Alkynyl Ketones
Logue, Marshall W.,Teng, Kelly
, p. 2549 - 2553 (1982)
Acyl chlorides couple with (1-alkynyl)tributylstannanes in the presence of catalytic amounts of palladium(II) or palladium(0) complexes to produce 1-alkynyl ketones in respectable yields.The couplings of isobutyryl, acetyl, benzoyl, and p-nitrobenzoyl chlorides with phenylethynyl-, (trimethylsilyl)ethynyl-, (carbomethoxy)ethynyl-, -1-propynyl>-, and (3,3-diethoxy-1-propynyl)tributylstannanes were investigated in the presence of tetrakis(triphenylphosphine)palladium(O), benzylchlorobis(triphenylphosphine)palladium(II), dichlorobis(triphenylphosphine)palladium(II), or phenyliodobis(triphenylphosphine)palladium(II).The reactions are highly selective in that only the alkynyl groups are transferred from the stannane.
MeOTf-Mediated Alkynylation of Selenoamides Leading to β-Methylselenenyl α,β-Unsaturated Ketones and Their Characterization
Murai, Toshiaki,Mutoh, Yuichiro,Kato, Shinzi
, p. 1993 - 1995 (2001)
(formula presented) β-Methylselenenyl α,β-unsaturated ketones were effectively synthesized by treating selenoamides with methyl triflate, followed by reaction with lithium acetylides. The reaction proceeded with high stereoselectivity to give exclusively Z-isomers. 77Se NMR studies and X-ray molecular structure analysis of β-methyselenenyl α,β-unsaturated ketones suggested that the products show 1,5-nonbonding interaction between the selenium atom and carbonyl oxygen atom.
Straightforward Novel One-Pot Enaminone and Pyrimidine Syntheses by Coupling-Addition-Cyclocondensation Sequences
Karpov, Alexei S.,Mueller, Thomas J. J.
, p. 2815 - 2826 (2003)
The coupling of acid chlorides 1 with terminal alkynes 2 using only one equivalent (!) of triethylamine under Sonogashira conditions followed by subsequent addition of primary or secondary amines 4 to the intermediate alkynones 3 represents a straight-for
C-C-bond formation in reactions of [(η5-C5H4SiMe3)2Ti(C?CR1)2]CuR with acyl chlorides and anhydrides
Frosch,Back,Lang
, p. 140 - 147 (2001)
The chemical behaviour of selected {[Ti](C?CR1)2}CuR complexes (1a: R1=SiMe3, R=CH3; 1b: R1=tBu, R=CH3; 1c: R1=tBu, R=C?CSiMe3) towards a number of different acyl chlorides and anhydrides is described. The reaction of 1a or 1b with R2C(O)Cl (2a: R2=CH3, 2b: R2=C6H5) produces the ketones R2C(O)R (4a: R=R2=CH3; 4b: R=CH3, R2=C6H5; 4c: R=C?CSiMe3, R2=CH3, 4d: R=C?CSiMe3, R2=C6H5) along with {[Ti](Cnequiv;CR1)2}CuCl (3a: R1=SiMe3, 3b: R1=tBu). However, on treatment of 1b or 1c with [CH3C(O)]2O (5a) the ketones 4a or 4c are formed along with the copper(I) acetate complex {[Ti](C?CtBu)2}CuOC(O)CH3 (6), while the reaction of 1b or 1c with CH3CO2H (5b) yields methane and 6. In addition, when 1b or 1c are reacted with maleic (7), phthalic (9a) or tetrachlorophthalic anhydride (9b) the copper(I) carboxylates {[Ti](C?CtBu)2}CuOC(O)-cis-CH=CH-C(O)R (8a: R=CH3, 8b: R=C?CSiMe3) and {[Ti](C?CtBu)2}CuOC(O)-C6H4-n Cln-2-C(O)R (10a: n=0, R=CH3; 10b: n=0, R=C?CSiMe3; 10c: n=4, R=C?CSiMe3) are produced, which upon addition of, e.g. HBr afford via cleavage of the copper-oxygen σ-bond {[Ti](C?CtBu)2}CuBr (3c) and the corresponding carboxylic acids cis-HO2C-CH=CH-C(O)CH3 (11a) or HO2C-C6H4-2-C(O)CH3 (11b), respectively.
Copper-catalyzed method for preparing aldehyde or ketone compound by oxidizing alcohol with oxygen as oxidizing agent and application
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Paragraph 0028-0030; 0064-0069, (2020/08/18)
The invention discloses a copper-catalyzed method for preparing an aldehyde or ketone compound by oxidizing alcohol with oxygen as an oxidizing agent. Reaction is performed in an organic solvent for 4-48 hours at room temperature by using copper salt and nitroxide free radicals as catalysts and oxygen or air as an oxidizing agent to efficiently oxidize an alcohol compound into the corresponding aldehyde or ketone compound. The method is simple to operate, free of chlorides corrosive to equipment, available in raw materials and reagents, mild in reaction conditions, wide in substrate universality, good in functional group compatibility, convenient in separation and purification, environmentally friendly in the whole process and free of pollution, and is a method suitable for industrial production.
Copper-Catalyzed Aminoboration from Hydrazones to Generate Borylated Pyrazoles
Tu, Kim N.,Kim, Scott,Blum, Suzanne A.
supporting information, p. 1283 - 1286 (2019/02/26)
Herein we report an aminoboration reaction that employs inexpensive, Earth-abundant, and commercially available Cu(OTf)2 as an effective catalyst in the direct addition of B-N σ bonds to C-C π bonds, generating borylated pyrazoles, which are us
Metal-Free Promoted CF2/CF3-Difunctionalization of Unactivated Alkenes
Li, Ming,Zhu, Xin-Yu,Qiu, Yi-Feng,Han, Ya-Ping,Xia, Yu,Wang, Cui-Tian,Li, Xue-Song,Wei, Wan-Xu,Liang, Yong-Min
supporting information, p. 2945 - 2950 (2019/04/27)
An operationally simple radical difluoroalkylation/trifluoromethylation and alkynylation of unactivated alkenes under mild conditions has been developed. Through this protocol, a series of CF2/CF3- substituted linear alkynyl ketones
Cascade and Effective Syntheses of Functionalized Tellurophenes
Karapala, Vamsi Krishna,Shih, Hong-Pin,Han, Chien-Chung
, p. 1550 - 1554 (2018/03/23)
A one-pot and transition-metal-catalyst-free synthetic strategy to construct functionalized tellurophenes has been developed. Substituted 1,1-dibromo-1-en-3-ynes are smoothly converted to tellurophenes with telluride salts in high yield via a series of cascade reactions through reductive debromination, hydrotelluration, nucleophilic cyclization, and aromatization. Close inspection of the results clearly showed that the reactivity of in situ prepared telluride salts are significantly influenced by the polarity of the solvent system and the electronic nature of the substituent on the enyne substrate. This method reports the first direct synthesis of 3-aryltellurophenes in high yields at room temperature. This novel reaction strategy is also found to be a promising synthetic method for multisubstituted tellurophenes and selenophenes.
