612-40-8Relevant academic research and scientific papers
Dual Nickel/Ruthenium Strategy for Photoinduced Decarboxylative Cross-Coupling of α,β-Unsaturated Carboxylic Acids with Cycloketone Oxime Esters
Gao, Ang,Jiang, Run-Chuang,Liu, Chuang-Chuang,Liu, Qi-Le,Lu, Xiao-Yu,Xia, Ze-Jie
supporting information, p. 8829 - 8842 (2021/06/30)
Herein, a dual nickel/ruthenium strategy is developed for photoinduced decarboxylative cross-coupling between α,β-unsaturated carboxylic acids and cycloketone oxime esters. The reaction mechanism is distinct from previous photoinduced decarboxylation of α,β-unsaturated carboxylic acids. This reaction might proceed through a nickelacyclopropane intermediate. The C(sp2)-C(sp3) bond constructed by the aforementioned reaction provides an efficient approach to obtaining various cyanoalkyl alkenes, which are synthetically valuable organic skeletons in organic and medicinal chemistry, under mild reaction conditions. The protocol tolerates many critical functional groups and provides a route for the modification of complex organic molecules.
Pd-Catalyzed decarboxylative cross-coupling reactions of epoxides with α,β-unsaturated carboxylic acids
Lu, Xiao-Yu,Li, Jin-Song,Wang, Shi-Qun,Zhu, Yu-Jing,Li, Yue-Ming,Yan, Lu-Yu,Li, Jia-Mei,Wang, Jin-Yu,Zhou, Hai-Pin,Ge, Xiu-Tao
supporting information, p. 11123 - 11126 (2019/09/20)
A Pd-catalyzed decarboxylative cross-coupling of α,β-unsaturated carboxylic acids with cyclic and acyclic epoxides has been developed. Both β-monosubstituted and β-disubstituted unsaturated carboxylic acids, as well as conjugated diene unsaturated carboxylic acids are suitable reaction substrates. Substituted homoallylic alcohols were obtained in moderate to good yields. The product was obtained as a mixture of diastereomers favoring the anti diastereomer of the cyclic epoxides. This work provides a method for the modification of complex organic molecules containing α,β-unsaturated carboxylic acids.
Oxidative cleavage of olefins by in situ-generated catalytic 3,4,5,6-tetramethyl-2-iodoxybenzoic acid/oxone
Moorthy, Jarugu Narasimha,Parida, Keshaba Nanda
, p. 11431 - 11439 (2015/02/05)
Oxidative cleavage of a variety of olefins to the corresponding ketones/carboxylic acids is shown to occur in a facile manner with 3,4,5,6-tetramethyl-2-iodobenzoic acid (TetMe-IA)/oxone. The simple methodology involves mere stirring of the olefin and catalytic amount (10 mol %) of TetMe-IA and oxone in acetonitrile-water mixture (1:1, v/v) at rt. The reaction mechanism involves initial dihydroxylation of the olefin with oxone, oxidative cleavage by the in situ-generated 3,4,5,6-tetramethyl-2-iodoxybenzoic acid (TetMe-IBX), and oxidation of the aldehyde functionality to the corresponding acid with oxone. Differences in the reactivities of electron-rich and electron-poor double bonds have been exploited to demonstrate chemoselective oxidative cleavage in substrates containing two double bonds.
Reductive electrochemical formation of 6H-dibenzo[b,d]pyran-6-one and 2-benzopyran-1(1H)-one
Batanero, Belen,Barba, Fructuoso,Barba, Isidoro,Elinson, Michail N.
, p. 82 - 85 (2014/01/06)
In the present Letter several carbolactones (oxidative products) are obtained under aprotic cathodic conditions in the preparative scaled electrolysis of 1,2-quinones in a divided electrochemical cell and in the presence of oxygen. When 9,10-phenanthrenequinone is reduced 6H-dibenzo[b,d]pyran-6-one and [1,1′-biphenyl]-2,2′-dicarboxylic acid are obtained as major products. In the reduction of 1,2-naphthoquinone, 2-benzopyran-1(1H)-one, and 2-(2-carboxyethenyl)-benzoic acid were formed as main products. The proposed mechanism to explain the formation of these and other products, that involves an electron-transfer reaction to the oxygen in air, is now discussed.
A PdCl2-ionic liquid brush assembly: An efficient and reusable catalyst for Mizoroki-Heck reaction in neat water
Shi, Xianying,Han, Xiaoyan,Ma, Wenjuan,Fan, Juan,Wei, Junfa
experimental part, p. 16 - 20 (2012/03/26)
An efficient and reusable heterogeneous catalytic assembly of PdCl 2 held in ionic liquid brushes has been synthesized and an environmentally-friendly procedure was developed for coupling aryl iodides with acrylic acid. These reactions were conducted in water under aerobic conditions with water-insoluble or even solid aryl iodides and they proceeded smoothly and cleanly without any organic co-solvent or other additives. A 0.5 mol% (based on Pd atom) dose of the catalyst was found to be sufficient for Mizoroki-Heck reaction. The catalyst is easily recovered post reaction, via simple filtration, and reused at least eight times without a noticeable loss of activity. The protocol has the advantages of excellent yield, environmental friendliness, and catalyst recyclability. Copyright
New synthetic methodology for construction of the 3,4-dihydroisoquinolinone skeleton: A key structure for isoquinoline alkaloids
Muejde, Berk,Oezcan, Sevil,Balci, Metin
scheme or table, p. 407 - 410 (2012/04/10)
We hereby report a new method for preparation of 3,4-dihydroisoquinolin- 1(2H)-one as well as isoquinolin-1(2H)-one skeleton starting from the methyl 2-(3-methoxy-3-oxopropyl)benzoate. The ester functionality, adjacent to the methylene, was regiospecifically converted to the desired acyl azide. The isocyanate was transformed into the monoisocyanate by Curtius rearrangement followed by trapping with aniline. The formed urea derivative was cyclized with NaH to give a 3,4-dihydroisoquinolin-1(2H)-one derivative. Incorporation of a double bond into the six-membered ring followed by removal of the substituent resulted in the formation of isoquinolin-1(2H)-one skeleton.
New synthetic methodology for construction of the 1,3,4,5-tetrahydro-2 H -1,3-benzodiazepin-2-one skeleton
Dengiz, Cagatay,Oezcan, Sevil,Sahin, Ertan,Balci, Metin
scheme or table, p. 1365 - 1370 (2010/07/02)
We hereby report a new synthetic methodology for construction of the 1,3,4,5-tetrahydro-2H-1,3-benzodiazepin-2-one skeleton. 2-(2-Carboxyethyl) benzoic acid was converted into the corresponding bis(acyl azide). Curtius rearrangement of the diazide followed by reaction with alcohols provided diurethane derivatives. Ring-closure reaction of the diurethanes with base resulted in formation of the 1,3-benzodiazepin-2-one skeleton. Georg Thieme Verlag Stuttgart · New York.
Some unusual reactions of Meldrum's acid. Synthesis of cinnamic acids, coumarins and 2-benzyl-1-indanone
Mahulikar,Mane
, p. 12 - 14 (2007/10/03)
The use of Meldrum's acid (1) in the synthesis of the substituted cinnamic acid 3 and malonic acid 4, the coumarins 8 and 9, and of 2-benzyl-1-indanone (13), is reported. The structure of benzylidene benzalmalonate is corrected to 14.
