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 reagent for efficient synthesis of nitriles from aldoximes using methoxymethyl bromide
ULUDAG, Nesimi,GIDEN, Ozge NUR
, p. 993 - 998 (2021/02/05)
This study outlines an efficient, high-yielding, and rapid method by which to access diverse nitriles from aldoximes with methoxymethyl bromide (MOM-Br) in THF. It represents the first application of MOM-Br as a deoximation reagent to synthesize nitriles. The reaction was performed at reflux to ensure excellent yield (79-96%) of the nitriles within 20-45 minutes. Furthermore, this method has been successfully applied to the synthesis of the synthesis precursor of aromatic, heteroaromatic, cyclic, and acyclic aliphatic.
NiFe2O4@SiO2@ZrO2/SO42-/Cu/Co nanoparticles: A novel, efficient, magnetically recyclable and bimetallic catalyst for Pd-free Suzuki, Heck and C-N cross-coupling reactions in aqueous media
Alavi G., Seyyedeh Ameneh,Nasseri, Mohammad Ali,Kazemnejadi, Milad,Allahresani, Ali,Hussainzadeh, Mahdi
, p. 7741 - 7757 (2021/05/13)
The novel heterogeneous bimetallic nanoparticles of Cu-Co were synthesized based on magnetic nanoparticles, and the magnetic nanocatalyst was characterized by XRD, FE-SEM, EDX mapping, BET, TEM, HRTEM, FTIR, TGA, and VSM. This catalyst was successfully applied as a recyclable magnetically catalyst in Heck, Suzuki, and C-N cross-coupling reactions with various aryl halides (iodides, bromides, and chlorides as challengeable substrates), with olefins, phenylboronic acid, and amines, respectively. We considered the rise of synergetic effects from the different Lewis acid and Br?nsted acid sites present in the catalyst. The catalyst was synthesized with cheap, available materials and a simple synthesis method. The catalyst can be separated easily using an external magnet. It was recycled for more than ten runs without a sensible loss of its catalytic activity, and no significant leaching of the Cu and Co quantity was observed. The significant benefits of the method are high-level generality, simple operation, and there are no heavy metals and toxic solvents. This is a quick, easy, efficacious and environmentally friendly protocol, and no by-products are formed in the reaction. These features make it an appropriate practical alternative protocol. In comparison with recent works, the other advantage of this catalyst is the synthesis of a wide variety of C-C and C-N bond derivatives (more than 40 derivatives). The other significant advantage is the low temperature of the reaction and the use of the least possible amount of the catalyst (0.003 g). The efficiency was good to excellent and the catalyst selectivity has been high. We aspire that our study inspires more interest to design novel catalysts based on using low-cost metal ions (such as cobalt and copper) in the cross-coupling reactions. This journal is
