22996-47-0Relevant academic research and scientific papers
A palladium-catalyzed C-H functionalization route to ketones: Via the oxidative coupling of arenes with carbon monoxide
Arndtsen, Bruce A.,Kinney, R. Garrison,Levesque, Taleah M.
, p. 3104 - 3109 (2020/03/27)
We describe the development of a new palladium-catalyzed method to generate ketones via the oxidative coupling of two arenes and CO. This transformation is catalyzed by simple palladium salts, and is postulated to proceed via the conversion of arenes into high energy aroyl triflate electrophiles. Exploiting the latter can also allow the synthesis of unsymmetrical ketones from two different arenes.
Controlled photo-flow oxidative reaction (UV-FOR) platform for ultra-fast phthalide and API synthesis
Aand, Dnyaneshwar,Karekar, Sanjeev,Mahajan, Bhushan,Pawar, Amit B.,Singh, Ajay K.
, p. 4584 - 4590 (2018/10/23)
An integrated photo-flow oxidative reaction (UV-FOR) platform approach is presented for the synthesis of phthalides. The current protocol is catalyst-free, and uses economical and abundant hydro-carbons and hydrocarbon derivatives such as benzoic acid, benzene, and xylene, as starting materials. The reaction is performed using oxygen as a green oxidant in a time- and labour-efficient manner. This integrated approach has been shown to be successful in making a UV-FOR platform suitable for the on-demand synthesis of phthalides and their further syntheses to 2-arylmethylbenzoic acids and arylogous Michael addition products under relatively mild conditions. The current protocol was further extended to the gram scale synthesis of an ischemic stroke-relevant active pharmaceutical ingredient (API), 3-N-butylphthalide (NBP), in a continuous flow process.
A general approach to intermolecular carbonylation of arene C-H bonds to ketones through catalytic aroyl triflate formation
Kinney, R. Garrison,Tjutrins, Jevgenijs,Torres, Gerardo M.,Liu, Nina Jiabao,Kulkarni, Omkar,Arndtsen, Bruce A.
, p. 193 - 199 (2018/02/06)
The development of metal-catalysed methods to functionalize inert C-H bonds has become a dominant research theme in the past decade as an approach to efficient synthesis. However, the incorporation of carbon monoxide into such reactions to form valuable ketones has to date proved a challenge, despite its potential as a straightforward and green alternative to Friedel-Crafts reactions. Here we describe a new approach to palladium-catalysed C-H bond functionalization in which carbon monoxide is used to drive the generation of high-energy electrophiles. This offers a method to couple the useful features of metal-catalysed C-H functionalization (stable and available reagents) and electrophilic acylations (broad scope and selectivity), and synthesize ketones simply from aryl iodides, CO and arenes. Notably, the reaction proceeds in an intermolecular fashion, without directing groups and at very low palladium-catalyst loadings. Mechanistic studies show that the reaction proceeds through the catalytic build-up of potent aroyl triflate electrophiles.
Catalytic Friedel-Crafts acylation: Magnetic nanopowder CuFe 2O4 as an efficient and magnetically separable catalyst
Parella, Ramarao,Naveen,Kumar, Amit,Babu, Srinivasarao Arulananda
, p. 1738 - 1742 (2013/03/28)
Catalytic regioselective Friedel-Crafts acylation of an array of anisoles/arenes with various acid chlorides using 5-20 mol % of magnetic nanopowder CuFe2O4 is reported. Unlike the conventional Friedel-Crafts reactions, which are catalyzed by moisture sensitive homogeneous catalysts/promoters, the nanopowder CuFe2O4 catalyst is moisture insensitive and the product/ketone-catalyst isolation is easily achieved using the magnetic properties of CuFe2O4.
MoO2Cl2 as a novel catalyst for Friedel-Crafts acylation and sulfonylation
de Noronha, Rita G.,Fernandes, Ana C.,Rom?o, Carlos C.
experimental part, p. 1407 - 1410 (2009/06/18)
The use of MoO2Cl2 as a novel catalyst for Friedel-Crafts acylation and sulfonylation is described. A series of aromatic ketones and sulfones were prepared in moderate to good yields using acyl chloride or sulfonyl chloride in the presence of MoO2Cl2 (20 mol %), under solvent-free conditions.
Esters as acylating reagent in a Friedel-Crafts reaction: Indium tribromide catalyzed acylation of arenes using dimethylchlorosilane
Nishimoto, Yoshihiro,Babu, Srinivasarao Arulananda,Yasuda, Makoto,Baba, Akio
supporting information; experimental part, p. 9465 - 9468 (2009/04/06)
(Chemical Equation Presented) The Friedel-Crafts acylation of arenes with esters by dimethylchlorosilane and 10 mol % of indium tribromide has been achieved. The key intermediate RCOOSi(Cl)Me2 is generated from alkoxy esters with the evolution of the corresponding alkanes. The scope of the alkoxy ester moiety was wide: tert-butyl, benzyl, allyl, and isopropyl esters were successful. In addition, we demonstrated the direct synthesis of the indanone intermediate 11 of salviasperanol from ester 10.
Synthesis and characterization of PET-based liquid crystalline copolyesters containing 6-oxynaphthalene-2-carboxylate and 6-oxyanthracene-2-carboxylate units
Hibbs, Michael R.,Vargas, Marian,Holtzclaw, Jeremy,Rich, Wendy,Collard, David M.,Schiraldi, David A.
, p. 7543 - 7551 (2007/10/03)
Copolymers of poly(ethylene terephthalate) (PET) containing 6-oxy-2-carboxyanthracene (OA) and 6-oxy-2-carboxynaphthalene (ON) structural units are prepared by reactive blending of acetoxyarenecarboxylic acid comonomers with PET. The new copolymers are ch
Acylierung von Aromaten mit Carbonsaeure-dihalogenphosphorsaeure-anhydriden
Effenberger, Franz,Koenig, Gerd,Klenk, Herbert
, p. 926 - 936 (2007/10/02)
Aryl ketones 4, 9 are formed in good yields without the addition of Friedel-Crafts catalysts from activated arenes (e. g. alkylbenzenes, anisole) and aryl- and alkylcarboxylic dihalophosphoric anhydrides 1, 2, and 7, 8, respectively.The anhydrides 7, 8 may be prepared in situ by mixing the respective carboxylic and dihalophosphoric anhydrides.This procedure is especially advantageous in care of the less stable compounds.
