4360-47-8Relevant articles and documents
Synthetic Methods and Reactions; 83. Sulfuryl Chloride Fluoride, a Mild Dehydrating Agent in the Preparation of Nitriles from Aldoximes
Olah, George A.,Narang, Subhash C.,Garcia-Luna, Armando
, p. 659 (1980)
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Highly diastereoselective aziridination of imines with trimethylsilyldiazomethane. Subsequent silyl substitution with electrophiles, ring opening, and metalation of C-silylaziridines - A cornucopia of highly selective transformations
Aggarwal, Varinder K.,Alonso, Emma,Ferrara, Marco,Spey, Sharon E.
, p. 2335 - 2344 (2002)
Treatment of a range of N-sulfonyl (Ts and SES) imines derived from aromatic, heteroaromatic, aliphatic, and unsaturated aldehydes with trimethylsilydiazomethane gave C-silylaziridines in good yield (32-83%) and with high diastereoselectivity in favor of the cis product (80:20-100:0). In contrast, an α-imino ester gave predominantly the trans-aziridine (89:11) in high yield (91%). The synthetic potential of C-silylaziridines was investigated. Treatment with F- (tetrabutylammonium triphenyldifluorosilicate was used) in the presence of aldehydes gave the α-hydroxyaziridines in high yield and high diastereoselectivity (86:14-98:2) for the newly created stereogenic center. Complete retention of configuration was observed in the substitution of the silyl group with electrophiles in all cases. Trapping with deuterium (using CDCl3 as electrophile) was also successful, but trapping with phosphate [using CIP(O)(OPh)2] and acetate (using Ac2O) was unsuccessful. In these latter cases ring opening by chloride and acetate, respectively, was observed. Further ring-opening reactions were effected using azide and thiolate nucleophiles and in all cases complete regioselectivity in favor of attack at the silyl-bearing carbon occurred. Complete regioselectivity was also observed in the carbonylative ring expansion using Co2(CO)8 to give a β-lactam. Treatment of cis-1-tosyl-2-phenyl/butyl-3-trimethylsilylaziridines with n-BuLi and subsequent quenching with MeI followed completely different pathways, depending on the 2-substituent. In the case of the 2-phenylaziridine, metalation was initiated α to the phenyl group and led finally to a fused tricyclic adduct with four stereogenic centers as a single diastereoisomer. In the case of the 2-butylaziridine, metalation occurred α to the silyl group and led to a trisubstituted silylaziridine, probably via an azirine intermediate.
Palladium N-methylimidazolium supported complexes as efficient catalysts for the Heck reaction
Altava, Belen,Burguete, M. Isabel,Garcia-Verdugo, Eduardo,Karbass, Naima,Luis, Santiago V.,Puzary, Amrit,Sans, Victor
, p. 2311 - 2314 (2006)
Different N-methylimidazolium supported ligands have been easily synthesized. The palladium complexes derived from those materials can be used for the catalysis of the Heck reaction giving excellent yields, selectivities and very good TON and TOF values. The supported Pd-pincer complexes show an increased stability, and provide a clear improvement in the recovery and reuse for the supported catalysts.
Pd(0) supported onto monolithic polymers containing IL-like moieties. Continuous flow catalysis for the Heck reaction in near-critical EtOH
Karbass, Naima,Sans, Victor,Garcia-Verdugo, Eduardo,Burguete, M. Isabel,Luis, Santiago V.
, p. 3095 - 3097 (2006)
Long-term stable Pd(0) catalysts can be easily supported onto polymeric monoliths containing methyl-imidazole moieties and the corresponding reactors based on these materials can be applied for the continuous Heck reaction in near-critical EtOH. The Royal Society of Chemistry 2006.
A new palladium heterogeneous complex (Pd-Gu@BOEH): chemoselective, phosphine-free and practical nanocatalyst in carbon–carbon cross-coupling reaction
Jafari, Fariba,Ghorbani-Choghamarani, Arash,Hasanzadeh, Neda
, p. 1033 - 1049 (2020/11/05)
Herein, boehmite nanoparticles were synthesized via combination of Al(NO3)3·9H2O and NaOH in aqueous solution. This nanomaterial converted to Pd-Gu@BOEH in several sequences. Pd-Gu@BOEH was used as efficient and recoverable nanocatalyst for the chemoselective C–C band formation such as Mizoroki–Heck and Suzuki–Miyaura reactions without any phosphine ligands or inert atmosphere. This catalyst has been characterized by several analyses such as EDS, WDX, SEM, XRD, FT-IR, TEM, TGA, AAS and BET. Also, obtained products from C–C coupling reactions were identified by NMR spectroscopy and their melting points. This catalyst was recycled in described reactions without palladium leaching. The reused catalyst was characterized by EDS, WDX, XRD, FT-IR and AAS analysis, which showed good stability during reaction process.
The Mizoroki-Heck reaction in mesoionic 1-butyl-3-methyltetrazolium-5-olate
Araki, Shuki,Hirashita, Tsunehisa,Kurabayashi, Hideaki
, (2021/10/12)
1-Butyl-3-methyltetrazolium-5-olate (1), a mesoionic compound, exists as a liquid at room temperature and can be used as a polar solvent for the Mizoroki-Heck reaction, wherein it has been proven to be a superior solvent to other solvents. The reaction of iodobenzene with ethyl acrylate in the presence of palladium acetate in mesoionic liquid 1 at 40 °C for 24 h gave ethyl cinnamate in 78% yield in the absence of ligands, while the use of other solvents, such as [bmim][BF4], [bmim][PF6], and DMF gave lower yields (43%, 37%, and 17%, respectively) under the same conditions. Heck-type coupling reactions of electron-deficient or electron-rich aryl iodides and bromobenzenes with olefins (15 examples, 7%–97%) were performed in 1. When a phosphine ligand was added to the reaction mixture, aryl bromides could be used, and the mesoionic liquid containing the catalysts could be reused at least five times.