19103-09-4Relevant 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.
Transition-metal-free carbonylation of aryl halides with arylboronic acids by utilizing stoichiometric CHCl3 as the carbon monoxide-precursor
Xu, Fangning,Li, Dan,Han, Wei
supporting information, p. 2911 - 2915 (2019/06/18)
Under transition-metal-free conditions, carbonylative Suzuki couplings of aryl halides with arylboronic acid using stoichiometric CHCl3 as the carbonyl source has been developed. The simple, efficient, and environmentally benign method was successfully applied to the synthesis of Fenofibric acid, naphthyl phenstatin, and carbon-13 labeled biaryl ketone.
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.
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.
Friedel-crafts benzoylation of alkylbenzenes with brazoic anhydride catalyzed by solid superacids
Nakamura, Hideo,Arata, Kazushi
, p. 1893 - 1896 (2007/10/03)
The liquid-solid phase benzoylation of mono-alkylbenzenes with methyl, ethyl, propyl, and butyl groups and xylenes was carried out with benzoic anhydride at 100-110°C over solid superacids: SO4/ZrO 2, WO3/ZrO2, and SO4/ HfO 2. The reactivity ratio obtained by the competitive method of reaction over WO3/ZrO2 was 1 to 4.6 for toluene to p-xylene and 1.1:10:1 among o-, m-, and p-xylenes, respectively. Although the SO4/ZrO2 catalyst gave high yields of 92 and 97% for toluene and ethylbenzene in a 3:7 distribution of o- and p-isomers, respectively, low yields were observed with propyl and butylbenzenes over the catalyst: that is, 5 and 2% for propylbenzene and isopropylbenzene, 14% for isobutylbenzene, and trace yields for butylbenzene, s-butylbenzene, and t-butylbenzene, respectively. The usual Friedel-Crafts benzoylation using AlCl3 was examined in the present alkylbenzenes in order to confirm the low reactivity of both propyl and butylbenzenes. The results were similar to those with the SO4/ZrO2 catalyst; that is, the yields at 0°C for 1 h were 37, 21, 6, 1, 0, 3, and 2% for toluene, ethylbenzene, propylbenzene, isopropylbenzene, butylbenzene, s-butylbenzene, and t-butylbenzene, respectively, showing an unexpected result where there was no distinction between homogeneous and heterogeneous conditions.
Perfluoroalkanesulfonic acid catalyzed acylations of alkylbenzenes: Synthesis of alkylanthraquinones
Effenberger,Buckel,Maier,Schmider
, p. 1427 - 1430 (2007/10/03)
The acylation of alkylbenzenes 1 with benzoyl chloride 2 and catalytic amounts of perfluorobutanesulfonic acid affords the corresponding 2-, 3-, and 4-alkylbenzophenones 3 with unusually high amounts of ortho products. Surprisingly, even tert-butylbenzene reacts under these reaction conditions without any acid catalyzed dealkylation. The yield of benzoylation of p-xylene 4 with benzoic acid in the presence of 5 mol% C4F9SO3H to give 2,5-dimethylbenzophenone 5 could significantly be improved from 14% to 90% by continuous removal of water formed during the acylation. Also in the preparation of alkylanthraquinones 7 by reaction of alkylbenzenes with phthalic anhydride, water removal is the decisive factor to obtain satisfactory yields for the second acylation, allowing to cyclize 6 with catalytic amounts (10 mol%) of CF3SO3H in organic solvents to the corresponding alkylanthraquinones 7.
RADIKALISCHE REAKTIONSWEGE BEI THERMISCH INDUZIERTEN UMSETZUNGEN VON ZIRCONOCENKOMPLEXEN
Erker, G.,Rosenfeldt, F.
, p. 1285 - 1292 (2007/10/02)
The formation of products 2, 3 and 4(a-l) from both the reaction of εta2-bezophenone zirconocene 1 with alkyl halides and the thermolysis of the α-(Cp2ZrCl)-substituted benzhydrylmethylether 9, the latter proceeding with anchimeric assistance of the metal, can be understood assuming a stepwise reaction path through radical intermediates.The proposed intermediate transition-metal benzophenone ketyl 12 exhibits a reaction pattern differing from analogous main-group-metal ketyls.
REVERSAL OF THE BENZOPHENONE REACTIVITY UPON η2 -COMPLEXATION TO BIS( η5 -CYCLOPENTADIENYL)ZIRCONIUM
Rosenfeldt, Frank,Erker, Gerhard
, p. 1637 - 1640 (2007/10/02)
Reversal of the carbonyl activity of benzophenone, serving as electron donor in single-electron transfer processes and acting as a proton acceptor through the 'carbonyl'carbon atom, is observed upon η2 -complexation to zirconocene.
