3508-77-8Relevant academic research and scientific papers
Concerted Catalysis in Tight Spaces: Palladium-Catalyzed Allylation Reactions Accelerated by Accumulated Active Sites in Mesoporous Silica
Motokura, Ken,Ikeda, Marika,Nambo, Masayuki,Chun, Wang-Jae,Nakajima, Kiyotaka,Tanaka, Shinji
, p. 2924 - 2929 (2017)
The surface of mesoporous silica was modified with a Pd–bisphosphine complex and/or a tertiary amine group for concerted acceleration of allylation reactions. Mesoporous-silica-supported catalysts with a 1.6 nm pore diameter showed higher performance than nonporous or larger mesoporous silica-supported catalysts owing to the accumulation of active sites into a confined space. For the case in which allyl alcohol was used in the reaction, the presence of a silanol group on the surface was quite effective: the turnover number of Pd was nine times greater than that of the homogeneous Pd complex.
Co-immobilization of a palladium-bisphosphine complex and strong organic base on a silica surface for heterogeneous synergistic catalysis
Motokura, Ken,Saitoh, Koki,Noda, Hiroto,Uemura, Yohei,Chun, Wang-Jae,Miyaji, Akimitsu,Yamaguchi, Sho,Baba, Toshihide
, p. 331 - 335 (2016)
Co-immobilization of a palladium-bisphosphine complex and a strong organic base, 1,4-diazabicyclo[2.2.2]octane (DABCO), on a silica support was successfully achieved. The new catalyst structure was characterized by X-ray photoelectron spectroscopy, solid-
Heterogeneous synergistic catalysis by a palladium complex and an amine on a silica surface for acceleration of the Tsuji-Trost reaction
Noda, Hiroto,Motokura, Ken,Miyaji, Akimitsu,Baba, Toshihide
, p. 8017 - 8020 (2012)
The cooperative surface-catalysis strategy of a Bronsted acid and an organic base can be extended to a metal complex and organic base pair. A silica-supported diaminopalladium complex and a tertiary amine were prepared and characterized. The Pd-catalyzed
Combining palladium complex and organic amine on graphene oxide for promoted Tsuji-Trost allylation
Zhao, Qingshan,Zhu, Yuanzhi,Sun, Zhen,Li, Yang,Zhang, Guoliang,Zhang, Fengbao,Fan, Xiaobin
, p. 2609 - 2616 (2015)
In this study, we develop a facile strategy to combine an organic amine with a palladium complex on graphene oxide (GO) as a cooperative catalyst for Tsuji-Trost allylation. A tertiary amine and palladium-diamine complex are simultaneously immobilized on
Accumulation of Active Species in Silica Mesopore: Effect of the Pore Size and Free Base Additives on Pd-catalyzed Allylation using Allylic Alcohol
Chun, Wang-Jae,Kawashima, Sae,Manaka, Yuichi,Motokura, Ken,Nambo, Masayuki
, (2020)
A mesoporous silica-supported Pd complex was prepared using various types of porous silica supports (pore size: 16–31 ?). The effects of the pore size and base additive properties on the catalytic allylation were investigated. The activity of the Pd-catal
The asymmetric synthesis of cyclopentane derivatives by palladium- catalyzed coupling of prochiral alkylboron compounds
Cho, Suk Young,Shibasaki, Masakatsu
, p. 3751 - 3754 (1998)
Treatment of the prochiral triflate 2a with Pd2(dba)3·CHCl3, (S)- (R)-BPPFOAc and K2CO3, in THF at 40°C, gave the cyclopentane derivative 10 in 58% yield and in 28% ee after oxidative work-up and benzoylation. Moreover, reaction of the prochiral triflate 2c with Pd2(dba)3·CHCl3, (S)-(R)-PPFA and K2CO3, in THF at 40°C, afforded the cyclopentane derivative 3b, with a quaternary carbon center, in 42% yield and in 31% ee after oxidative work-up.
Decarboxylative Annulation of α-Amino Acids with β-Ketoaldehydes
Paul, Anirudra,Thimmegowda,Galani Cruz, Thiago,Seidel, Daniel
supporting information, p. 602 - 604 (2018/02/09)
Indolizidine and quinolizidine derivatives are readily assembled from l-proline or (±)-pipecolic acid and β-ketoaldehydes via a decarboxylative annulation process. These reactions are promoted by acetic acid and involve azomethine ylides as reactive intermediates.
Silica Support-Enhanced Pd-Catalyzed Allylation Using Allylic Alcohols
Motokura, Ken,Ikeda, Marika,Kim, Minjune,Nakajima, Kiyotaka,Kawashima, Sae,Nambo, Masayuki,Chun, Wang-Jae,Tanaka, Shinji
, p. 4536 - 4544 (2018/09/21)
Although allylation using allylic alcohol is an environmentally-friendly method because of water being the sole byproduct in such reactions, allylic alcohol is one of the most difficult allylating agents in Pd-catalyzed allylation of nucleophiles. In this study, we successfully developed a mesoporous silica-supported Pd complex as an efficient catalyst for the allylation of nucleophiles using allylic alcohols as allylating agents. The allylic alcohol is activated by the silanol group on the support surface, which easily undergoes a π-allylpalladium intermediate formation. The catalytic activity of the supported Pd complex was ca. 9 times higher than that of its homogeneous precursor Pd complex. A highest turnover number of 4500 based on Pd was achieved. Various nucleophiles and allylic alcohol derivatives could be used as substrates. Not only the detailed catalyst structure but also the reaction mechanism including the concerted activation of allylic alcohol by the Pd complex and silanol were investigated by several spectroscopic techniques, such as Pd K-edge XAFS, solid-state NMR, and in-situ FT-IR measurements.
Phase-transfer Tsuji—Trost allylation of CH-acids with the assistance of palladium complexes with bidentate PIII—N—PIII ligands
Vasil′ev,Aladzheva,Bykhovskaya
, p. 661 - 665 (2017/09/11)
The Tsuji—Trost allylation of CH acids, in particular, those of the YCH2CO2Et type (Y = CO2Et, C(O)Me, CN), with allylic acetates in the K2CO3—DMF system in the presence of palladium catalysts with ligands RN(PPh2)2 (R = Ph, Pri, c-C6H11) is accomplished.
Highly efficient Tsuji-Trost allylation in water catalyzed by Pd-nanoparticles
Llevot,Monney,Sehlinger,Behrens,Meier
supporting information, p. 5175 - 5178 (2017/07/12)
Palladium nanoparticles stabilized by poly(vinylpyrrolidone) catalyze Tsuji-Trost allylations in water with very high turnover numbers. The di-allylation of methylene active compounds and the allylation of bio-based phenols was performed in high yield. The allylation of lignin showed a high selectivity towards the phenolic OH groups.
