38630-01-2Relevant academic research and scientific papers
Carbon-sulfur bond formation of challenging substrates at low temperature by using Pd-PEPPSI-IPent
Sayah, Mahmoud,Organ, Michael G.
supporting information; experimental part, p. 11719 - 11722 (2011/11/29)
Aryl thiols made cool and quick: The coupling of alkyl, aryl, and silyl thiols to hindered, deactivated aryl bromides and chlorides has been achieved under the most mild temperatures yet reported (i.e., room temperature to 40°C). The bulk afforded by the di-2,6-(3-propylphenyl)imidazolium-derived Pd-PEPPSI-IPent catalyst is believed to actively promote the critical reductive elimination step of the catalytic cycle, thereby eliminating the formation of poisonous off-cycle dimeric resting states that have plagued Pd-catalyzed sulfination reactions.
Copper-catalyzed Ullmann coupling under ligand- and additive-free conditions. Part 2: S-Arylation of thiols with aryl iodides
Buranaprasertsuk, Pongchart,Chang, Joyce Wei Wei,Chavasiri, Warinthorn,Chan, Philip Wai Hong
, p. 2023 - 2025 (2008/09/19)
S-Arylation of a wide variety of substituted aryl and aliphatic thiols with aryl halides catalyzed by copper iodide under mild ligand- and additive-free conditions (nBu4NBr, PhMe, NaOH, reflux, 22 h) is accomplished in good to excellent product yields (up to 96%).
Studies on nucleophilic substitution reactions with cyclopentadienyliron complexes of some chloroarenes and nitorarenes and syntheses of substituted arenes by demetallation of the substitution products
Abd-El-Aziz, A.S.,Lee, C. C.,Piorko, A.,Sutherland, R. G.
, p. 95 - 108 (2007/10/02)
Nucleophilic substitution reactions with the cyclopentadienyliron (CpFe) complex of m- or p-dichlorobenzene with carbanion nucleophiles derived from ethyl acetoacetate (EAA), dibenzoylmethane (DBM) or diacetylmethane (DAM) were found to give only monosubstitution as previously observed for the CpFe complex of o-dichlorobenzene.Reaction of the CpFe complex of 2,6-dimethylchlorobenzene (XIVa) or 2,6-dimethylnitorbenzene (XIVb) with nucleophiles derived from ammonia, dimethylamine, n-butylamine, pyrrolidine, ethanol, phenol, o-thiocresol and EAA all gave SNAr products, without significant steric hindrance.However, no reaction was observed in the treatment of XIVa or XIVb with DBM, suggesting that only with a bulky nucleophile such as that derived from DBM were steric hindrance effects sufficiently large to prevent an SNAr reaction with XIVa or XIVb.Pyrolytic sublimation of the various SNAr products was found to cause decomposition in some cases, but in most instances, demetallation took place giving rise to substituted arenes.New substituted arenes prepared in this way in the present work included RC6H4CH(COC6H5)2, with R = p-CH3, o-Cl, m-Cl or p-Cl, and 2,6-(CH3)2C6H3Y, with Y = CH3(CH2)3NH, C2H5O or o-CH3C6H4S.
