637-50-3Relevant articles and documents
Bumgardner, Jwerks
, p. 431 (1968)
HETEROPOLY ANION-ASSISTED Rh CATALYSIS REVEALED IN THE HOMOGENEOUS SELECTIVE HYDROGENATION
Urabe, Kazuo,Tanaka, Yoshiyuki,Izumi, Yusuke
, p. 1595 - 1596 (1985)
When coupled with lithium salt of heteropoly acid, the Wilkinson complex RhCl(PPh3)3 catalyst became very active and selective for the semihydrogenation of alkyne to alkene and, more interestingly, exhibited sharp substrate-selectivity in hydrogenation of substituted alkenes.
The N-Methylpyrrolidone (NMP) Effect in Iron-Catalyzed Cross-Coupling with Simple Ferric Salts and MeMgBr
Mu?oz, Salvador B.,Daifuku, Stephanie L.,Sears, Jeffrey D.,Baker, Tessa M.,Carpenter, Stephanie H.,Brennessel, William W.,Neidig, Michael L.
, (2018)
The use of N-methylpyrrolidone (NMP) as a co-solvent in ferric salt catalyzed cross-coupling reactions is crucial for achieving the highly selective, preparative scale formation of cross-coupled product in reactions utilizing alkyl Grignard reagents. Desp
Isomerization of 3-phenyl-1-propene (allylbenzene) over base catalysts
Marinas,Aramendia,Borau,Jimenez,Marinas,Urbano
, p. 556 - 559 (2002)
The isomerization of 3-phenyl-1-propylene (allylbenzene) to 1-phenyl-1-propylene (β-methylstyrene) (cis + trans) was studied as a new test reaction for base catalysts. The injection of pure trans-β-methylstyrene (without catalyst) only yielded 1% of the other isomer (cis-βmethylstyrene). The injection of pure trans-β-methylstyrene, in the presence of catalysts, yielded small quantities of allylbenzene and cis-β-methylstyrene. Poisoning of the catalyst with CO2 led to a sharp decrease in activity. The trans/cis ratio was ～ six for all the catalysts.
Identifying and Evading Olefin Isomerization Catalyst Deactivation Pathways Resulting from Ion-Tunable Hemilability
Dodge, Henry M.,Kita, Matthew R.,Chen, Chun-Hsing,Miller, Alexander J. M.
, p. 13019 - 13030 (2020)
Hemilabile ligands are found in many leading organometallic catalysts, but it can be challenging to tune the degree of hemilability in a particular catalyst. This work explores the impact of cation-tunable hemilability on the speciation of iridium(III) pincer-crown ether catalysts during high-activity olefin isomerization. Under conditions where strong cation-macrocycle interactions are fostered and terminal olefin has been consumed, labilization of the aza-crown ether group leads to an η6-arene complex, wherein the pincer ligand is metallated at a different position. Arene complexes of styrene, naphthalene, and mesitylene were independently synthesized and found to exhibit diminished catalytic activity for allylbenzene isomerization. In response to these findings, a previously unreported catalyst bearing a synthetically modified pincer ligand was designed, resulting in a refined system that maintains high activity even when arene complexes are formed.
Regioselective Deaminative Allylation of Aliphatic Amines via Dual Cobalt and Organophotoredox Catalysis
Sekino, Tomoyuki,Sato, Shunta,Yoshino, Tatsuhiko,Kojima, Masahiro,Matsunaga, Shigeki
supporting information, p. 2120 - 2124 (2022/03/27)
Despite the rapid progress in C-C bond-forming reactions using Katritzky salts, their deaminative allylation remains a challenge. Inspired by the metallaphotoredox-catalyzed allylic substitution regime, here, we report the deaminative allylation of Katritzky salts via cobalt/organophotoredox dual catalysis. This cross-electrophile coupling enables regioselective allylation using a variety of allylic esters, overcoming the substrate limitations of reported protocols. Mechanistic studies indicate the involvement of a π-allyl cobalt complex as a radicalophile that mediates C-C bond formation.
Switching the Reactivity of Palladium Diimines with “Ancillary” Ligand to Select between Olefin Polymerization, Branching Regulation, or Olefin Isomerization
Jones, Glen R.,Basbug Alhan, Hatice E.,Karas, Lucas J.,Wu, Judy I.,Harth, Eva
supporting information, p. 1635 - 1640 (2020/11/30)
Coordinating solvents are commonly employed as ancillary ligands to stabilize late transition metal complexes and are conventionally considered to have little effect on the reaction products. Our work identifies that the presence of ancillary ligand in Pd-diimine catalyzed polymerizations of α-olefins can drastically alter reactivity. The addition of different amounts of acetonitrile allows for switching between distinct reaction modes: isomerization–polymerization with high branching (0 equiv.), regular chain-walking polymerization (1 equiv.), and alkene isomerization with no polymerization (>20 equiv.). Optimization of the isomerization reaction mode led to a general set of conditions to switch a wide variety of diimine complexes into efficient alkene isomerization catalysts, with catalyst loading as low as 0.005 mol %.
