16692-58-3Relevant academic research and scientific papers
Palladium-catalyzed: Ortho -halogen-induced deoxygenative approach of alkyl aryl ketones to 2-vinylbenzoic acids
Ram, Shankar,Sharma, Ajay Kumar,Chauhan, Arvind Singh,Das, Pralay
, p. 10674 - 10677 (2020/10/02)
The 2-vinylbenzoic acids have wide applications in the field of polymer chemistry and are key precursors for the synthesis of important bioactive molecules. Herein, an ortho-halogen-induced deoxygenative approach for the generation of 2-vinylbenzoic acids from alkyl aryl ketones by palladium catalysis is discovered and explored. This approach requires no base or stoichiometric additives and can be carried out through a simple one-step process. Furthermore, the present reaction is scalable up to one-gram scale. The commercially available palladium on carbon (5 wt%) was used as a heterogeneous catalyst and showed excellent recyclability (5 times) without significant loss in catalytic activity. Pleasingly, under our optimized conditions, the alpha alkyl substituted 2-iodoacetophenones exhibit good diastereoselectivity and predominantly (E)-2-vinylbenzoic acids were obtained with good to excellent yields.
Cobalt-Catalyzed Coupling of Benzoic Acid C?H Bonds with Alkynes, Styrenes, and 1,3-Dienes
Nguyen, Tung Thanh,Grigorjeva, Liene,Daugulis, Olafs
supporting information, p. 1688 - 1691 (2018/01/15)
A method for cobalt-catalyzed, carboxylate-directed functionalization of arene C?H bonds is reported. Alkynes, styrenes, and 1,3-dienes can be coupled with benzoic acids to provide cyclic products in good yields. The reactions proceed in the presence of a
An Easy-to-Machine Electrochemical Flow Microreactor: Efficient Synthesis of Isoindolinone and Flow Functionalization
Folgueiras-Amador, Ana A.,Philipps, Kai,Guilbaud, Sébastien,Poelakker, Jarno,Wirth, Thomas
, p. 15446 - 15450 (2017/11/10)
Flow electrochemistry is an efficient methodology to generate radical intermediates. An electrochemical flow microreactor has been designed and manufactured to improve the efficiency of electrochemical flow reactions. With this device only little or no supporting electrolytes are needed, making processes less costly and enabling easier purification. This is demonstrated by the facile synthesis of amidyl radicals used in intramolecular hydroaminations to produce isoindolinones. The combination with inline mass spectrometry facilitates a much easier combination of chemical steps in a single flow process.
Stereoselective synthesis of hydroxy stilbenoids and styrenes by atom-efficient olefination with thiophthalides
Mitra, Prithiba,Shome, Brateen,Ranjan De, Saroj,Sarkar, Anindya,Mal, Dipakranjan
, p. 2742 - 2752 (2012/11/07)
The synthesis of stilbenoids and styryl carboxylic acids is accomplished with high E-stereoselectivity by olefination of aldehydes with thiophthalides under basic conditions. The olefination is highly atom-efficient as it only loses elemental sulfur during the reaction. This olefination, in conjunction with retro Kolbe-Schmitt reaction, allows facile synthesis of E-hydroxystilbenoids with minimal employment of protecting groups. This study also discloses two important findings: formation of i) 4-methylsulfanyl isocoumarins and ii) an 2-arylindenone. The Royal Society of Chemistry 2012.
Stereospecific Formation of 2-benzoic Acids in an Unusual Reaction of Thiophthalides with Aldehydes
Mal, Dipakranjan,Majumdar, Gita,Pal, Ranjan
, p. 1115 - 1116 (2007/10/02)
The reaction of thiophthalides 1 with aldehydes 3 in the presence of lithium tert-butoxide at -60 deg C to 25 deg C results in the stereospecific formation of only trans 2-(alk-1'-enyl)benzoic acids 4 in fairly good yields in one-pot operations.This react
