79204-44-7Relevant academic research and scientific papers
COtab: Expedient and Safe Setup for Pd-Catalyzed Carbonylation Chemistry
Collin, Hugo P.,Reis, Wallace J.,Nielsen, Dennis U.,Lindhardt, Anders T.,Valle, Marcelo S.,Freitas, Rossimiriam P.,Skrydstrup, Troels
supporting information, p. 5775 - 5778 (2019/08/26)
Bench-stable tablets (COtabs) have been developed for the rapid and safe production of carbon monoxide. The tablets can be made in less than 5 min without the use of a glovebox and only require a stock solution of an amine base to liberate a specific quantity of CO in a two-chamber system. The COtabs were tested in five different carbonylation reactions and provided similar yields compared to literature procedures. Finally, a gram-scale reaction was conducted, as well as 13C-isotope labeling of the anticancer drug, olaparib.
Synthesis of bis(heteroaryl) ketones by removal of benzylic CHR and CO groups
Maji, Arun,Rana, Sujoy,Akanksha,Maiti, Debabrata
, p. 2428 - 2432 (2014/03/21)
A copper-catalyzed method for synthesis of diaryl ketones (Ar-CO-Ar′) through removal of benzylic -CH2-, -CO-, and -CHR- groups from Ar-CO-CXR-Ar′ has been discovered. A number of symmetrical and unsymmetrical heterocyclic ketones, which are usually difficult to synthesize, can be prepared in good to excellent yields. This method was applied to the synthesis of the nonsteroidal anti-inflammatory drug suprofen (47 % yield over three steps). Based on preliminary mechanistic and kinetic studies, an active Cu/O2 species is proposed to mediate the rearrangement reaction. Snip snip: A copper-catalyzed method for synthesis of diaryl ketones by removal of benzylic CH2, CO, and CHR groups has been discovered. A number of symmetrical and unsymmetrical heterocyclic ketones, which are usually difficult to synthesize, can be prepared in good to excellent yields. Preliminary mechanistic studies indicate that an active Cu/O2 species mediates the rearrangement. Copyright
Ligand-free Pd-catalyzed carbonylative cross-coupling reactions under atmospheric pressure of carbon monoxide: Synthesis of aryl ketones and heteroaromatic ketones
Li, Hongling,Yang, Min,Qi, Yanxing,Xue, Jijun
supporting information; experimental part, p. 2662 - 2667 (2011/06/25)
The carbonylative Suzuki cross-coupling reactions of boronic acids with aryl iodides catalyzed by Pd2(dba)3 as a ligand-free catalyst under atmospheric pressure of carbon monoxide has been firstly developed. Under mild reaction conditions, a broad range of aryl/heteroaryl iodides and aryl/heteroaryl boronic acids were selectively coupled to afford the corresponding diaryl ketones in good to excellent yields at low catalyst loadings (0.05 to 2 mol-%). Moreover, the catalyst can also be recycled. The carbonylative Suzuki cross-coupling reactions of boronic acids with aryl iodides catalyzed by Pd2(dba)3 as a ligand-free catalyst under an atmosphere of carbon monoxide has been developed. A broad range of aryl/heteroaryl iodides and aryl/heteroaryl boronic acids were selectively coupled to afford the corresponding diaryl ketones in good to excellent yields. The catalyst can also be recycled.
Weinreb amide based building blocks for convenient access to analogues of phenstatin
Sivaraman, Balasubramaniam,Aidhen, Indrapal Singh
scheme or table, p. 4991 - 5003 (2010/11/05)
Bifunctional synthetic equivalents containing a Weinreb amide as one of the functionalities have been synthesized from commercially available o-, m-, and p-toluic acid. These bifunctional building blocks enabled efficient C-C bond formation through Wittig reaction with simple and functionalized aldehydes on one hand and a clean nucleophilic addition of 3,4,5-trimethoxy phenylmagnesium bromide onto the Weinreb amide functionality on the other hand, therebypaving way for an efficient and convenient synthesis of novel analogues of phenstatin with highly functionalized appendages. Further addition of various aryl or heteroarylmagnesium bromides onto theWeinreb amide functionality provided a general strategy for synthesizing unsymmetrical diaryl ketones conjugated to a monosaccharide moiety for the first time.
A general synthesis of diarylketones by means of a three-component cross-coupling of aryl and heteroaryl bromides, carbon monoxide, and boronic acids
Neumann, Helfried,Brennfuehrer, Anne,Beller, Matthias
experimental part, p. 3645 - 3652 (2009/04/11)
Pd(OAc)2/di-1-adamantyl-n-butylphosphine (cataCXium A) is highly active in the three-component Suzuki carbonylation and represents the most general catalyst system reported up to now. A broad range of aryl/heteroaryl bromides and aryl boronic acids can be coupled to the corresponding diarylketones at low catalyst loadings.
An efficient and practical sequential one-pot synthesis of suprofen, ketoprofen and other 2-arylpropionic acids
Neumann, Helfried,Brennfuehrer, Anne,Beller, Matthias
experimental part, p. 2437 - 2442 (2009/10/06)
A novel sequential double carbonylation to synthesize anti-inflammatory drugs such as Ketoprofen and Suprofen has been developed. Starting from easily available aryl halides and arylboronic acids a one-pot carbonylative Suzuki and hydroxycarbonylation reaction sequence proceeds in good selectivity and high yield in the presence of the palladium/cataCXium A catalyst system. Applying optimized conditions different 2-arylpropionic acids were synthesized in good yields.
Asymmetric Hydroformylation Catalyzed by Homogeneous and Polymer-Supported Platinum Complexes Containing Chiral Phosphine Ligands
Parrinello, Giovanni,Stille, J. K.
, p. 7122 - 7127 (2007/10/02)
A complex of Pt(II) containing the chiral ligand (2S,4S)-N-(tert-butoxycarbonyl)-4-(diphenylphosphino)-2-pirrolidine in the presence of stannous chloride catalyzed the hydroformylation of a variety of prochiral olefins.Although the branched/normal (b/n) ratios were low (ca. 0.5), high ee's were achieved in the hydroformylation of styrene (70-80percent), p-isobutylstyrene (80percent), 2-vinylnaphthalene (77percent), 2-ethenyl-6-methoxynaphthalene (81percent), 4-(2-thienylcarbonyl)styrene (78percent), vinyl acetate(82percent), N-vinylphthalimide (73percent), methyl methacrylate (60percent), and norbornene (60percent).When the hydroformylation of styrene, 2-ethenyl-6-methoxynaphthalene, and vinyl acetate with PtCl2/SnCl2 was carried out in the presence of triethyl orthoformate, enantiomerically pure acetals were obtained.The hydroformylation in the presence of ethyl orthoformate also could be carried out by using a catalyst containing the PtCl2/SnCl2 complex bound to 60-μm beads composed of cross-linked polystyrene.
Synthesis of Functionalized Styrenes via Palladium-Catalyzed Coupling of Aryl Bromides with Vinyl Tin Reagents
McKean, D. R.,Parrinello, G.,Renaldo, A. F.,Stille, J. K.
, p. 422 - 424 (2007/10/02)
Highly functionalized styrene derivatives have been synthesized in a single step by the palladium-catalyzed coupling of aryl bromides with tributylethenylstannane.Aryl bromides substituted with electron-withdrawing groups couple rapidly under the reaction conditions while bromides containing electron-donating substituents require further addition of catalyst for complete conversion. 1,4-Dibromobenzene can be coupled in a highly selective fashion with either 1 or 2 equiv of tin reagent to give 4-bromostyrene or diethenylbenzene, respectively.
