1564-53-0Relevant academic research and scientific papers
Pd-Catalysed carbonylative Suzuki-Miyaura cross-couplings using Fe(CO)5under mild conditions: generation of a highly active, recyclable and scalable ‘Pd-Fe’ nanocatalyst
Zhu, Zhuangli,Wang, Zhenhua,Jian, Yajun,Sun, Huaming,Zhang, Guofang,Lynam, Jason M.,McElroy, C. Robert,Burden, Thomas J.,Inight, Rebecca L.,Fairlamb, Ian J. S.,Zhang, Weiqiang,Gao, Ziwei
supporting information, p. 920 - 926 (2021/02/09)
The dual function and role of iron(0) pentacarbonyl [Fe(CO)5] has been identified in gaseous CO-free carbonylative Suzuki-Miyaura cross-couplings, in which Fe(CO)5supplied COin situ, leading to the propagation of catalytically active Pd-Fe nanoparticles. Compared with typical carbonylative reaction conditions, CO gas (at high pressures), specialised exogenous ligands and inert reaction conditions were avoided. Our developed reaction conditions are mild, do not require specialised CO high pressure equipment, and exhibit wide functional group tolerance, giving a library of biaryl ketones in good yields.
Palladium-catalyzed synthesis of diaryl ketones from aldehydes and (hetero)aryl halides via C-H bond activation
Wakaki, Takayuki,Togo, Takaya,Yoshidome, Daisuke,Kuninobu, Yoichiro,Kanai, Motomu
, p. 3123 - 3128 (2018/04/14)
We developed a palladium-catalyzed C-H transformation that enabled the synthesis of ketones from aldehydes and (hetero)aryl halides. The use of picolinamide ligands was key to achieving the transformation. Heteroaryl ketones, as well as diaryl ketones, were synthesized in good to excellent yields, even in gram-scale, using this reaction. Results of density functional theory (DFT) calculations support the C-H bond activation pathway.
Extending the scope of the carbonyl facilitated triplet excited state towards visible light excitation
Rajagopal, Shinaj K.,Nagaraj,Deb, Somadrita,Bhat, Vinayak,Sasikumar, Devika,Sebastian, Ebin,Hariharan, Mahesh
, p. 19120 - 19128 (2018/08/07)
A series of extended π-conjugated benzophenone analogs was synthesized through a facile Lewis-acid catalyzed Friedel-Crafts reaction in order to exploit the integral triplet state properties of benzophenone. Extending the π-conjugated plane of the phenyl ring of benzophenone allowed tuning of the excitation wavelength from the far-UV end (～260 nm) to the visible spectrum (～446 nm). Compared to benzophenone, significant red-shifts in the absorption (up to 450 nm in solution) with high photostability were observed for the synthesized benzophenone analogs. As is evident from the density functional theory calculations, expansion of the ring size of the aromatic part of the benzophenone analogs induces a decrease in the HOMO-LUMO gap. The considerable extension of the electron density to the carbonyl group in the LUMO substantiates the triplet nature associated with the benzophenone analogs. By virtue of the properties of the carbonyl functionality, an apparent increase in the triplet quantum yield (ΦT = 5.4% to 87.7%) was observed for the benzophenone analogs when compared to the corresponding bare polyaromatic hydrocarbon. The spin orbit coupling was computationally estimated for the benzophenone analogs to propose pathways for the observed intersystem crossing process. The plausibility to photoexcite the aromatic-ring-fused benzophenone frameworks for triplet activation in the visible range opens the door for a new class of materials for photonic application.
P -Selective (sp2)-C-H functionalization for an acylation/alkylation reaction using organic photoredox catalysis
Pandey, Ganesh,Tiwari, Sandip Kumar,Singh, Bhawana,Vanka, Kumar,Jain, Shailja
supporting information, p. 12337 - 12340 (2017/11/20)
p-Selective (sp2)-C-H functionalization of electron rich arenes has been achieved for acylation and alkylation reactions, respectively, with acyl/alkylselenides by organic photoredox catalysis involving an interesting mechanistic pathway.
An efficient combination of Zr-MOF and microwave irradiation in catalytic Lewis acid Friedel-Crafts benzoylation
Doan, Tan L. H.,Dao, Thong Q.,Tran, Hai N.,Tran, Phuong H.,Le, Thach N.
supporting information, p. 7875 - 7880 (2016/05/24)
A zirconium-based metal-organic framework, an effective heterogeneous catalyst, has been developed for the Friedel-Crafts benzoylation of aromatic compounds under microwave irradiation. Constructed by a Zr(iv) cluster and a linker 1,4-bis(2-[4-carboxyphenyl]ethynyl)benzene (H2CPEB), the MOF, possessing large pores and high chemical stability, was appropriate for the enhancement of Lewis acid activity under microwave irradiation. The reaction studies demonstrated that the material could give high yields for a few minutes and maintain its reactivity and structure over several cycles.
Erbium trifluoromethanesulfonate catalyzed Friedel-Crafts acylation using aromatic carboxylic acids as acylating agents under monomode-microwave irradiation
Tran, Phuong Hoang,Hansen, Poul Erik,Nguyen, Hai Truong,Le, Thach Ngoc
, p. 612 - 618 (2015/02/19)
Erbium trifluoromethanesulfonate is found to be a good catalyst for the Friedel-Crafts acylation of arenes containing electron-donating substituents using aromatic carboxylic acids as the acylating agents under microwave irradiation. An effective, rapid and waste-free method allows the preparation of a wide range of aryl ketones in good yields and in short reaction times with minimum amounts of waste.
Synthesis of industrially important aromatic and heterocyclic ketones using hierarchical ZSM-5 and Beta zeolites
Kore, Rajkumar,Srivastava, Rajendra,Satpati, Biswarup
, p. 129 - 141 (2015/09/28)
Hierarchical ZSM-5 and Beta zeolites were investigated in the synthesis of wide range of industrially important aromatic/heterocyclic ketones by Friedel-Crafts acylation and benzoylation reactions. For comparative study, conventional ZSM-5 and Beta, and amorphous mesoporous Al-MCM-41 were investigated. Hierarchical zeolites were prepared by multi-ammonium structure directing agents whereas conventional zeolites were prepared by mono-ammonium structure directing agents. Among the catalysts investigated in this study, hierarchical Beta exhibited the highest reactant conversion in the acylation and benzoylation reactions. In this study, the systematic assessment of the catalytic activity of acid catalysts for wide range of aromatic and heterocyclic compounds is shown under one umbrella. To the best of our knowledge, these reactions over hierarchical zeolites (ZSM-5 and Beta) are reported here for the first time. Structure activity relationship is explained based on the physico-chemical properties, molecular size, reactivity of reactants, and reaction mechanism. Catalysts can be easily recovered and reused with negligible loss in the catalytic activity.
Microwave-assisted facile and rapid friedel-crafts benzoylation of arenes catalyzed by bismuth trifluoromethanesulfonate
Tran, Phuong Hoang,Hansen, Poul Erik,Pham, Thuy Thanh,Huynh, Vy Thanh,Huynh, Vy Hieu,Thi Tran, Thao Du,Huynh, Thanh Van,Le, Thach Ngoc
, p. 2921 - 2929 (2014/10/15)
The catalytic activity of metal triflates was investigated in Friedel-Crafts benzoylation under microwave irradiation. Friedel-Crafts benzoylation with benzoyl chloride of a variety of arenes containing electron-rich and electron-poor rings using bismuth triflate under microwave irradiation is described. This method allows the preparation of aryl ketones under solventless conditions in good to excellent yields and short reaction time. Bismuth triflate was easily recovered and reused five times without significant loss of the catalytic activity.
Expedient carbonylation of aryl halides in aqueous or neat condition
Ang, Wei Jie,Lo, Lee-Chiang,Lam, Yulin
, p. 8545 - 8558 (2014/12/11)
An expedient and versatile, microwave-assisted procedure for the carbonylation of aryl halides with boronic acids, alcohols or amines in water or under neat conditions has been developed. The reaction is catalyzed by fluorous, oxime-based palladacycle 1 that shows an excellent recyclable property and low levels of Pd leaching. To demonstrate the usefulness of the protocol, we applied it to the preparation of compounds of pharmaceutical interest, including a precursor of the reverse transcriptase inhibitor, niacin, benzocaine and butamben.
Polyaniline-supported zinc oxide (ZnO) nanoparticles: An active and stable heterogeneous catalyst for the Friedel-Crafts acylation reaction
Rezaei, Seyed Jamal Tabatabaei,Nabid, Mohammad Reza,Hosseini, Seyedeh Zahra,Abedi, Mahvash
experimental part, p. 1432 - 1444 (2012/04/17)
We report herein the synthesis of zinc oxide (ZnO) nanoparticles incorporating a polyaniline (PANI) matrix in aqueous medium and its catalytic performance toward Friedel-Crafts acylation reactions. The acylation reactions demonstrate that polyaniline/ nano-ZnO composites are very active catalysts and are able to activate the reactant at ambient temperature. The obtained nanocatalyst was characterized by Fourier transform-infrared, scanning electron microscopy, transmission electron microscopy, Brunauer-Emmett-Teller, X-ray diffraction, and particle-size analysis techniques. The catalyst was reusable for five cycles without appreciable loss in activity. Copyright Taylor & Francis Group, LLC.
