78633-37-1Relevant articles and documents
Synthesis of benzoxazoles via the copper-catalyzed hydroamination of alkynones with 2-aminophenols
Oshimoto, Kohei,Tsuji, Hiroaki,Kawatsura, Motoi
, p. 4225 - 4229 (2019)
We describe herein the synthetic method to benzoxazole derivatives via the copper-catalyzed hydroamination of alkynones with 2-aminophenols. The method produced a wide variety of functionalized benzoxazole derivatives in good yields. Preliminary mechanistic experiments revealed that the reaction would proceed through the copper-catalyzed hydroamination of alkynones and the sequential intramolecular cyclization of β-iminoketones/elimination of acetophenone promoted by the copper catalyst.
Bifunctional phosphine ligand-enabled gold-catalyzed direct cycloisomerization of alkynyl ketones to 2,5-disubstituted furans
Hu, Xiaojun,Zhou, Bingwei,Jin, Hongwei,Liu, Yunkui,Zhang, Liming
supporting information, p. 7297 - 7300 (2020/07/14)
An efficient synthesis of 2,5-disubstituted furans directly from alkynyl ketones has been developed via tandem gold(i)-catalyzed isomerization of alkynyl ketones to allenyl ketones and cycloisomerization. The key to the success of this chemistry is the use of a biphenyl-2-ylphosphine ligand featuring a critical remote tertiary amino group.
Ionic liquid-mediated benzoyl transfer-coupling in the Suzuki and Sonogashira reactions and aryl transfer-coupling by decarbonylative Heck reaction, using N-Benzoyl-saccharin (NBSac) as reagent
Malunavar, Shruti S.,Sutar, Suraj M.,Prabhala, Pavankumar,Kalkhambkar, Rajesh G.,Laali, Kenneth K.
, (2020/05/18)
The efficacy of N-benzoyl-saccharin (NBSac) as reagent for selective benzoyl transfer-coupling in the Suzuki reaction in BMIM-IL/[PAIM][NTf2] as solvent/base, and in the Sonogashira reaction employing guanidinium-IL (GIL) as solvent, are demonstrated. Decarbonylative aryl transfer-coupling occurs in the Heck reaction employing GIL as solvent. The reactions are catalyzed by Pd(OAc)2 or NiCl2(dppp), are performed under mild conditions in good yields, and have the potential for recycling/reuse of the IL solvent. Collectively, these methods provide facile access to diverse libraries of diarylketones, keto-ethynes and diaryl-ethenes.
Novel (N-heterocyclic carbene)Pd(pyridine)Br2 complexes for carbonylative Sonogashira coupling reactions: Catalytic efficiency and scope for arylalkynes, alkylalkynes and dialkynes
Ibrahim, Mansur,Malik, Imran,Mansour, Waseem,Sharif, Muhammad,Fettouhi, Mohammed,El Ali, Bassam
, (2018/03/05)
New N,N′-substituted imidazolium salts and their corresponding dibromidopyridine–palladium(II) complexes were successfully synthesized and characterized. Reactions of palladium bromide with the newly synthesized N,N′-substituted imidazolium bromides (2a a
Palladium-catalyzed Sonogashira coupling of amides: Access to ynones: Via C-N bond cleavage
Cui, Ming,Wu, Hongxiang,Jian, Junsheng,Wang, Hui,Liu, Chao,Daniel, Stelck,Zeng, Zhuo
, p. 12076 - 12079 (2016/10/13)
The first palladium-catalyzed Sonogashira coupling of amides has been developed, which proceeds via a selective cleavage of the N-acylsaccharin C-N bond. Notably, the new approach employs N-acylsaccharins as coupling partners to give ynones in good to excellent yield. This protocol can be efficiently utilized in the synthesis of a broad array of ynones under low catalyst loading and Cu-free conditions.
Palladium-catalyzed carbonylative coupling of aryl iodides and benzyl acetylenes to 3-alkylidenefuran-2-ones under mild conditions and its density functional theory modeling
Wu, Xiao-Feng,Jiao, Haijun,Neumann, Helfried,Beller, Matthias
, p. 16177 - 16185 (2013/02/22)
A general and efficient method for the palladium-catalyzed carbonylative coupling of aryl iodides to benzyl acetylenes has been developed. Various furanones have been prepared in excellent yields from their corresponding benzyl acetylenes at room temperat
Cobalt(III) complex catalyzed aerobic oxidation of propargylic alcohols
Blay, Gonzalo,Cardona, Luz,Fernandez, Isabel,Pedro, Jose R.
, p. 3329 - 3332 (2008/09/21)
An o-phenylenebis(N′-methyloxamidate) cobalt(III) complex works as an efficient catalyst for the oxidation of propargylic alcohols to the corresponding α,β-acetylenic carbonyl compounds, in the presence of pivalaldehyde, under an atmospheric pressure of m
Two-step synthesis of β-alkyl chalcones and their use in the synthesis of 3,5-diaryl-5-alkyl-4,5-dihydropyrazoles
Cox, Christopher D.,Breslin, Michael J.,Mariano, Brenda J.
, p. 1489 - 1493 (2007/10/03)
We report a simple and efficient two-step synthesis of variously substituted β-alkyl chalcones (7) from the corresponding Weinreb amide and a terminal alkyne, and that these chalcones are useful intermediates for the synthesis of medicinally interesting 3,5-diaryl-5-alkyl-4,5-dihydropyrazoles (6). The current methodology allows for the incorporation of many substitution patterns not available from the few previously reported approaches to compounds in this class.
Carbonylation of Organic Halides in the Presence of Terminal Acetylenes; Novel Acetylenic Ketone Synthesis
Kobayashi, Toshiaki,Tanaka, Masato
, p. 333 - 334 (2007/10/02)
Aryl, heterocyclic, and vinylic halides react with carbon monoxide and terminal acetylenes at 120 deg C or below and 80 atm or below in the presence of triethylamine and a catalytic amount of a palladium(II) complex to form acetylenic ketones in 46.7 - 92.0 percent yield.
