86535-76-4Relevant academic research and scientific papers
Visible-light-mediated photocatalytic cross-coupling of acetenyl ketones with benzyl trifluoroborate
Zhang, Lingchun,Chu, Yanle,Ma, Peizhi,Zhao, Shujuan,Li, Qiaoyan,Chen, Boya,Hong, Xuejiao,Sun, Jun
supporting information, p. 1073 - 1077 (2020/02/22)
In this report, we describe a simple visible light-triggered Barbier-type reaction by employing acetenyl ketones with benzyl trifluoroborates. Through a radical-radical cross-coupling process, this photocatalytic protocol furnished a wide range of tertiary propargyl alcohols. Mechanistic investigation indicated that proton-coupled electron transfer (PCET) might be involved in the photochemical transformations.
Spiroannulation of Oxindoles via Aryne and Alkyne Incorporation: Substituent-Diverted, Transition-Metal-Free, One-Pot Access to Spirooxindoles
Samineni, Ramesh,Madapa, Jaipal,Srihari, Pabbaraja,Mehta, Goverdhan
, p. 3119 - 3122 (2017/06/23)
A "product control via substrate design" strategy has been conceptualized and implemented to harness the potential of aryne and activated alkyne insertions into oxindoles to readily and efficiently furnish pharmacophoric indano- and cyclopentannulated spirooxindole scaffolds in an operationally straightforward, one-pot, transition-metal-free protocol.
Aryl-palladium-NHC complex: Efficient phosphine-free catalyst precursors for the carbonylation of aryl iodides with amines or alkynes
Zhang, Chunyan,Liu, Jianhua,Xia, Chungu
supporting information, p. 9702 - 9706 (2015/02/19)
A series of aryl-palladium-NHC compounds was prepared according to the reported methods and their catalytic activity in the carbonylation of aryl iodides to synthesize α-keto amides and alkynones was examined. These practical aryl-palladium-NHC complexes have shown highly efficient catalyzed carbonylation and Sonogashira carbonylation reactions, with high turnover number in synthesis of α-keto amides (TON = 4300) and in synthesis of alkynones (TON = 980).
Palladium-catalyzed carbonylative sonogashira coupling of aryl bromides via tert -butyl isocyanide insertion
Tang, Ting,Fei, Xiang-Dong,Ge, Zhi-Yuan,Chen, Zhong,Zhu, Yong-Ming,Ji, Shun-Jun
, p. 3170 - 3175 (2013/06/27)
A simple and efficient palladium-catalyzed carbonylative Sonogashira coupling via tert-butyl isocyanide insertion has been developed, which demonstrates the utility of isocyanides in intermolecular C-C bond construction. This methodology provides a novel pathway for the synthesis of alkynyl imines which can undergo simple silica gel catalyzed hydrolysis to afford alkynones. The approach is tolerant of a wide range of substrates and applicable to library synthesis.
Catalytic syntheses of N-heterocyclic ynones and ynediones by in situ activation of carboxylic acids with oxalyl chloride
Boersch, Christina,Merkul, Eugen,Mueller, Thomas J. J.
, p. 10448 - 10452 (2011/12/05)
Breaking the bottleneck: α-Keto carboxylic acids and N-heterocyclic carboxylic acids are activated in situ with oxalyl chloride then catalytically alkynylated to give ynediones and N-heterocyclic ynones efficiently in a one-pot fashion. 5-Acylpyrazoles and 2-phenylaminopyrimidines, potentially interesting for pharmaceutical applications, are readily synthesized in concise one-pot, three-component syntheses. Copyright
Pd-catalyzed carbonylative reactions of aryl iodides and alkynyl carboxylic acids via decarboxylative couplings
Park, Ahbyeol,Park, Kyungho,Kim, Yong,Lee, Sunwoo
supporting information; experimental part, p. 944 - 947 (2011/04/24)
Alkynyl carboxylic acids reacted with aryl iodides under a CO atmosphere in the presence of a palladium catalyst to produce α,β-alkynyl aryl ketones in good yields. The maximum turnover number was 16 800. The desired carbonylative coupling was formed from phenyl propiolic acid without any formation of a noncarbonylative coupling product in the absence of CuI. However, the reaction with alkyl-substituted alkynyl carboxylic acids required CuI as a cocatalyst for high yield.(Figure Presented)
The synthesis of highly substituted isoxazoles by electrophilic cyclization: An efficient synthesis of valdecoxib
Waldo, Jesse P.,Larock, Richard C.
, p. 9643 - 9647 (2008/03/17)
(Chemical Equation Presented) A large number of functionally substituted 2-alkyn-1-one O-methyl oximes have been cyclized under mild reaction conditions in the presence of ICl to give the corresponding 4-iodoisoxazoles in moderate to excellent yields. The resulting 4-iodoisoxazoles undergo various palladium-catalyzed reactions to yield 3,4,5-trisubstituted isoxazoles, including valdecoxib.
