2007
DOI: 10.1002/adsc.200600305
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Activation of CCl Bonds in Chloroalkanes by Nickel Oxide Nanoparticles: Formation of Tetrasubstituted Ammonium Salts from Tertiary Amines

Abstract: Nickel oxide nanoparticles, readily available and easy to handle, were found to be an effective catalyst in the catalytic activation of C À Cl bonds in chloroalkanes. Coupling reactions of chloroalkanes and tertiary amines in the presence of the nickel oxide nanoparticle catalyst gave moderate to high yields of quaternary ammonium salts depending upon the amines.

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Cited by 14 publications
(5 citation statements)
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“…As early as 1986, Mas and Sola synthesized Et 3 NCH 2 ClCl and used [Et 3 NCH 2 Cl] + as a cationic ligand to successfully synthesize [Et 3 NCH 2 Cl] 2 [PtCl 4 ] . The cationic ligand used was synthesized by the Menshutkin Reaction, which is the reaction of tertiary amine and halogenated hydrocarbon. Sui’s group successfully synthesized [BrCH 2 CH 2 N­(CH 3 ) 3 ]­[PbBr 3 ] based on the quasi-spherical theory, which undergoes a reversible phase transition from Cc to Pnma at 302 K . By means of halogen substitution engineering, not only can the phase transition temperature be changed but also the bandgap can be regulated.…”
Section: Introductionmentioning
confidence: 99%
“…As early as 1986, Mas and Sola synthesized Et 3 NCH 2 ClCl and used [Et 3 NCH 2 Cl] + as a cationic ligand to successfully synthesize [Et 3 NCH 2 Cl] 2 [PtCl 4 ] . The cationic ligand used was synthesized by the Menshutkin Reaction, which is the reaction of tertiary amine and halogenated hydrocarbon. Sui’s group successfully synthesized [BrCH 2 CH 2 N­(CH 3 ) 3 ]­[PbBr 3 ] based on the quasi-spherical theory, which undergoes a reversible phase transition from Cc to Pnma at 302 K . By means of halogen substitution engineering, not only can the phase transition temperature be changed but also the bandgap can be regulated.…”
Section: Introductionmentioning
confidence: 99%
“…Thus, the recently reported activation of the C-Cl bonds of CH 2 Cl 2 in the presence of pyridine and Ni(0) nanoparticles required 100 1C and 10 h reaction time. 4 As part of our studies on the coordination chemistry of P,O-and P,N-functional phosphines, 5 we were interested in isolating Co(I) complexes, inter alia because of their possible involvement in the cobalt-catalyzed homogeneous carbonylation of methanol, 6 and unexpectedly discovered that CH 2 Cl 2 can be used as a methylation reagent under mild reaction conditions.…”
mentioning
confidence: 99%
“…Single-electron oxidation/deprotonation of the intermediate D and radical-polar transformation by the [Ir IV ] species produce the intermediate G and then elimination with the aid of bases to produce intermediate H . Sequentially, intermediate H undergoes dehydrochloration and addition with the •CHCl 2 radical B in the presence of bases, giving the intermediate J . Finally, intermediate J is converted to product 2 through the single-electron oxidation, dechloration twice, and hydrolysis cascade …”
mentioning
confidence: 99%
“…Sequentially, intermediate H undergoes dehydrochloration and addition with the •CHCl 2 radical B in the presence of bases, giving the intermediate J . Finally, intermediate J is converted to product 2 through the single-electron oxidation, dechloration twice, and hydrolysis cascade …”
mentioning
confidence: 99%