162611-86-1Relevant articles and documents
Synthesis of [carbonyl-11C]acetophenone via the Stille cross-coupling reaction of [1-11C]acetyl chloride with tributylphenylstannane mediated by Pd2(dba)3/P(MeNCH2CH2)3N·HCl
Arai, Takuya,Kato, Koichi,Zhang, Ming-Rong
, p. 4788 - 4791 (2009)
The Stille cross-coupling reaction of [1-11C]acetyl chloride with tributylphenylstannane leading to [carbonyl-11C]acetophenone was studied with the goal of developing a new 11C-labeling method for positron emission tomography tracer synthesis. The coupled product [carbonyl-11C]acetophenone was synthesized using the Pd2(dba)3/P(MeNCH2CH2)3N·HCl system with a 60-61% radiochemical conversion from [1-11C]acetyl chloride (decay-corrected, n = 3).
Synthesis of 11C-/13C-Ketones by Suzuki Coupling
Rahman, Obaidur,Kihlberg, Tor,Langstroem, Bengt
, p. 474 - 478 (2004)
Aryl triflates, methyl- or arylboronic acids, and a low concentration of [11C]carbon monoxide were employed on small scale in the syntheses of fifteen 11C-labelled ketones using palladium-mediated Suzuki coupling reactions. The reagents were confined in a micro-autoclave and heated at 150 °C for 5 min. The reaction required the presence of LiBr, but no additional base. The 11C-labelled products were obtained with decay-corrected radiochemical yields in the range 10-70% and with high specific radioactivity (150-640 GBq/μmol). The radiochemical purity of the final products exceeded 98%. One 13C-substituted ketone ([ 13C]-2′-benzonaphthone) was prepared and analysed by NMR spectroscopy for confirmation of the labelling position. The reference compound 2′-benzonaphthone was prepared by a palladium-catalysed reaction between sodium tetraphenylborate and 2-naphthoyl chloride. 2-Thienyl p-tolyl ketone, 4-nitrophenyl 2-thienyl ketone and 2-naphthyl 2-thienyl ketone were prepared by reactions between thiophene-2-boronic acid and the corresponding acid chlorides. The presented approach is novel and seems to be an efficient method for the synthesis of a wide range of 11C- as well as 13C-labelled ketones. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
Palladium-mediated 11C-carbonylative cross-coupling of alkyl/aryl iodides with organostannanes: An efficient synthesis of unsymmetrical alkyl/aryl [11C-carbonyl]ketones
Karimi, Farhad,Barletta, Julien,Langstroem, Bengt
, p. 2374 - 2378 (2005)
[11C]Carbon monoxide in low concentration, palladium complexes, alkyl/aryl iodides, and organostannanes are utilized in the synthesis of twenty alkyl [carbonyl-11C]ketones. The activated palladium(0) species [Pd{P(o-Tol)3}
Synthesis of [11C]/(13C)amines via carbonylation followed by reductive animation
Rahman, Obaidur,Kihlberg, Tor,Langstroem, Bengt
, p. 1612 - 1616 (2007/10/03)
Twelve 11C-labelled amines were prepared via 11C-carbonylation followed by reductive amination. The 11C-carbonylation was performed in the presence of tetrakis(triphenylphosphine)palladium using aryl iodides or aryl trifla
[11C]Carbon monoxide in the palladium-mediated synthesis of 11C-labelled ketones
Lidstroem, Pelle,Kihlberg, Tor,Langstrom, Bengt
, p. 2701 - 2706 (2007/10/03)
[11C]Carbon monoxide has been used in the palladium-mediated synthesis of [carbonyl-11C]ketones. Methyl iodide, vinylic and arylic halides and trifluoromethanesulfonates (triflates) have been coupled with tin reagents with insertion of [11C]carbon monoxide at very low concentrations (10-100 nmol[11C]CO in a total volume of 10 ml). The labelled products are obtained in 36-62% isolated decay-corrected radiochemical yields within 30 min of the end of radionuclide production. In order to use [11C]carbon monoxide efficiently, a gas handling system has been developed which allows the radioactive gas to recirculate through the reaction media. The reactions are performed using a one pot procedure. The best results are achieved with mixed tin reagents containing an unsaturated transferable substituent and Pd(AsPh3)4. In a typical experiment starting from 25 GBq of [11C]carbon dioxide, 4.2 GBq (47%) of [carbonyl-11C]acetophenone 1 is obtained 30 min after the end of radionuclide production. The specific radioactivity of 1 is 91 GBq μmol-1. [carbonyl-13C]Benzophenone 6 has been synthesised using the same approach to verify the position of the label.
