54545-91-4Relevant academic research and scientific papers
Highly efficient ambient-temperature copper-catalyzed atom-transfer radical addition (ATRA) in the presence of free-radical initiator (V-70) as a reducing agent
Pintauer, Tomislav,Eckenhoff, William T.,Ricardo, Carolynne,Balili, Marielle N. C.,Biernesser, Ashley B.,Noonan, Sean J.,Taylor, Matthew J. W.
, p. 38 - 41 (2009)
Highly efficient, ambient-temperature, copper-catalyzed Atom Transfer Radical Addition (ATRA) of polyhalogenated compounds to alkenes in the presence of free radical initiator 2,2' -azobis (4-methoxy-2,4-dimethyl valeronitrile)(V-70)as a reducing agent was reported. The discrepancies between the alkene conversion and percent yield were mostly due to competing free-radical polymerization. ATRA of polyhalogenated compounds to monomers that are highly active in free-radical polymerization was not successful at 60 ° C when AIBN was used as radical initiator. The V-70 was proved to be very effective reducing agent, enabling selective formation of the monoadduct with α -olefins and highly active monomers such as methyl acrylate, methyl methacrylate, and vinyl acetate. The methodology for catalyst regeneration in copper-mediated ATRA in the presence of V-70 as a reducing agent also worked very well in the addition of CCl4 and CBr4 to highly active vinyl acetate.
Photoinitiated ambient temperature copper-catalyzed atom transfer radical addition (ATRA) and cyclization (ATRC) reactions in the presence of free-radical diazo initiator (AIBN)
Balili, Marielle Nicole C.,Pintauer, Tomislav
experimental part, p. 3060 - 3066 (2011/05/13)
The use of UV light in copper-catalyzed atom transfer radical addition (ATRA) and cyclization (ATRC) reactions of various (poly)halogenated compounds to highly active alkenes in the presence of AIBN is reported. Radicals generated from photodecomposition of AIBN efficiently regenerated the copper(i) complex at ambient temperature enabling ATRA of CCl4 and CBr4 with catalyst loadings as low as 0.05 mol-%. The desired monoadduct was obtained in lower yields in the ATRA of less active halogenated compounds, which was mostly due to incomplete alkene conversions. Ambient temperature ATRA of CCl 4 to various 1,6-dienes followed by sequential ATRC was also performed in the presence of UV light using [CuII(TPMA)Cl][Cl] complex and AIBN. High yields of the 5-exo-trig cyclic product were obtained for all dienes with preferential formation of the cis isomer. The Royal Society of Chemistry 2011.
Atom transfer radical addition (ATRA) catalyzed by copper complexes with tris[2-(dimethylamino)ethyl]amine (Me6TREN) ligand in the presence of free-radical diazo initiator AIBN
Eckenhoff, William T.,Pintauer, Tomislav
experimental part, p. 4909 - 4917 (2011/06/27)
In this article, we focus on the evaluation of tris[2-(dimethylamino)ethyl] amine (Me6TREN) ligand in copper catalyzed ATRA in the presence of free-radical diazo initiator AIBN (2,2′-azobis(2-methylpropionitrile)). The addition of carbon tetrac
Highly efficient copper-mediated atom-transfer radical addition (ATRA) in the presence of reducing agent
Eckenhoff, William T.,Garrity, Sean T.,Pintauer, Tomislav
, p. 563 - 571 (2008/12/22)
The synthesis, characterization and exceptional activity of Cu I(TPMA)Br [TPMA = tris(2-pyridylmethyl)amine] and [Cu II(TPMA)Br][Br] complexes in ATRA reactions of polybrominated compounds to alkenes in the presence of reducing agent
