63476-27-7Relevant academic research and scientific papers
Heck arylation of allyl alcohol catalyzed by Pd(0) nanoparticles
Tarnowicz, Stanis?awa,Alsalahi, Waleed,Mieczyńska, Ewa,Trzeciak, Anna M.
, p. 5605 - 5612 (2017)
Pd(0) nanoparticles ca. 2 nm in diameter were obtained by the reduction of PdCl2 and Pd(OAc)2 in water at 80 °C in the presence of a PVP-stabilizing polymer. Pd(0) NPs were successfully used in the Heck coupling of allyl alcohol with iodo- and bromobenzenes. Iodobenzenes reacted under solventless conditions or in DMF solution producing 3-arylpropanals and 2-arylpropanals as the main products. The same products were obtained in the reaction of bromobenzene in TBAB as the reaction medium. The stability of Pd(0) NPs was evidenced in recycling experiments. Similar Heck coupling results were also obtained with the palladium compounds PdCl2(cod) and Pd(OAc)2 under the same conditions.
Binuclear Pd(I)-Pd(I) Catalysis Assisted by Iodide Ligands for Selective Hydroformylation of Alkenes and Alkynes
Zhang, Yang,Torker, Sebastian,Sigrist, Michel,Bregovi?, Nikola,Dydio, Pawe?
supporting information, p. 18251 - 18265 (2020/11/02)
Since its discovery in 1938, hydroformylation has been thoroughly investigated and broadly applied in industry (>107 metric ton yearly). However, the ability to precisely control its regioselectivity with well-established Rh- or Co-catalysts has thus far proven elusive, thereby limiting access to many synthetically valuable aldehydes. Pd-catalysts represent an appealing alternative, yet their use remains sparse due to undesired side-processes. Here, we report a highly selective and exceptionally active catalyst system that is driven by a novel activation strategy and features a unique Pd(I)-Pd(I) mechanism, involving an iodide-assisted binuclear step to release the product. This method enables β-selective hydroformylation of a large range of alkenes and alkynes, including sensitive starting materials. Its utility is demonstrated in the synthesis of antiobesity drug Rimonabant and anti-HIV agent PNU-32945. In a broader context, the new mechanistic understanding enables the development of other carbonylation reactions of high importance to chemical industry.
A novel consecutive three-component Heck-isomerization-Wittig sequence by way of in situ generated aldehydes
Panther, Jesco,Roehrich, Adalbert,Mueller, Thomas J. J.
, p. 297 - 311 (2013/09/24)
A novel consecutive three-component four step synthesis of 5-(hetero)arylpent-2-enoates has been disclosed. Various (hetero)aryl iodides can be coupled with allyl alcohol under Heck conditions to give 3-(hetero)arylpropionaldehyde intermediates, which were transformed without isolation with in situ generated stabilized phosphorus ylides to furnish 5-(hetero)arylpent-2-enoates in moderate to excellent yield. This one-pot procedure circumvents the isolation of sensitive aldehydes and phosphorus ylides as intermediates and finally gives the product isomers with good to excellent E/Z and β/α selectivity. ARKAT-USA, Inc.
