3032-81-3Relevant articles and documents
Palladium-Catalyzed Decarbonylative Iodination of Aryl Carboxylic Acids Enabled by Ligand-Assisted Halide Exchange
Boehm, Philip,Cacherat, Bastien,Lee, Yong Ho,Martini, Tristano,Morandi, Bill
supporting information, p. 17211 - 17217 (2021/07/02)
We report an efficient and broadly applicable palladium-catalyzed iodination of inexpensive and abundant aryl and vinyl carboxylic acids via in situ activation to the acid chloride and formation of a phosphonium salt. The use of 1-iodobutane as iodide source in combination with a base and a deoxychlorinating reagent gives access to a wide range of aryl and vinyl iodides under Pd/Xantphos catalysis, including complex drug-like scaffolds. Stoichiometric experiments and kinetic analysis suggest a unique mechanism involving C?P reductive elimination to form the Xantphos phosphonium chloride, which subsequently initiates an unusual halogen exchange by outer sphere nucleophilic substitution.
INHIBITORS OF METALLO-BETA-LACTAMASES PRODUCED BY MULTIDRUG-RESISTANT BACTERIA
-
Paragraph 0053-0054, (2021/05/29)
A compound having Formula I or its derivative may inhibit metallo-beta-lactamases. An investigation studying the effects of the compounds was provided by the invention of the activities of all subclasses (B1, B2, and B3) metallo-beta-lactamases. The compounds can be used for a pharmaceutical product with the ability to restore an anti-bacterial activity of a beta-lactam antibiotic, thereby treating and preventing a bacterial infection in an animal or human subject.
Sterically controlled iodination of arenes via iridium-catalyzed C-H borylation
Partridge, Benjamin M.,Hartwig, John F.
supporting information, p. 140 - 143 (2013/03/28)
A mild method to prepare aryl and heteroaryl iodides by sequential C-H borylation and iodination is reported. The regioselectivity of this process is controlled by steric effects on the C-H borylation step and is complementary to existing methods to form aryl iodides. The iodination of boronic esters has potential for the synthesis of radiolabeled aryl iodides, as demonstrated by the concise synthesis of a potential tracer for SPECT imaging.
New method of synthesis and biological evaluation of some combretastatin A-4 analogues
Malysheva, Yulia B.,Combes, Sebastien,Fedorov, Alexey Yu.,Knochel, Paul,Gavryushin, Andrei E.
supporting information; experimental part, p. 1205 - 1208 (2012/06/29)
A series of novel combretastatin A-4 analogues was synthesized in 36-64% yields by Negishi cross-coupling reaction under mild conditions. The prepared compounds exhibit good cytotoxicity against HBL100 epithelial cell lines (IC50=0.022-10.31 ). Georg Thieme Verlag Stuttgart · New York.
Cobalt-catalyzed preparation of arylindium reagents from aryl and heteroaryl bromides
Adak, Laksmikanta,Yoshikai, Naohiko
experimental part, p. 7563 - 7568 (2011/11/12)
A cobalt-bathophenanthroline catalyst has been developed for the direct preparation of a variety of arylindium reagents from the corresponding aryl and heteroaryl bromides in the presence of indium metal and lithium chloride. The thus-formed arylindium reagents undergo efficient palladium-catalyzed cross-coupling reactions with aryl iodides, tolerating various functional groups including hydroxy and free amino groups.
Preparation of polyfunctional zinc organometallics using an Fe- or Co-catalyzed Cl/Zn-exchange
Melzig, Laurin,Diene, Coura R.,Rohbogner, Christoph J.,Knochel, Paul
supporting information; experimental part, p. 3174 - 3177 (2011/08/06)
A new Fe- or Co-catalyzed Cl/Zn-exchange reaction allows the direct transformation of aryl, heteroaryl, and also alkyl chlorides into the corresponding zinc reagents. The method tolerates functional groups such as a nitrile or an ester. Remarkably, secondary and tertiary alkyl chlorides are suitable substrates for the Cl/Zn exchange.
Nucleophilic Displacement in Polyhalogenoaromatic Compounds. Part 11. Kinetics of Protiodeiodination of Iodoarenes in Dimethyl Sulphoxide-Methanol
Bolton, Roger,Moore, Clive,Sandall, John P.B.
, p. 1593 - 1598 (2007/10/02)
The rates of methoxide-ion induced protiodeiodination of a number of polychloroiodobenzenes and their derivatives have been measured in dimethyl sulphoxide-methanol (9:1 v/v; 323.2 K).The true reagent under these conditions appears to be the dimethyl sulphoxide anion, and the rates of reaction in some cases appear to approach that expected of a diffusion controlled process.This corresponds to a major decrease in the efficacy of further activating substituents in the aromatic system, altough deactivating groups such as p-OMe still show large effects.Chlorine promotes protiodeiodination in the order of efficiency o-Cl > m-Cl > p-Cl; the trifluoromethyl group activates displacement in the order o-CF3 > p-CF3 > m-CF3, although with much less difference between isomeric sites. o-Nitro-groups promote protiodeiodination whereas the p-nitro-group encourages methoxydeiodination.No evidence of methoxydeiodination was found in attack of the polychloroiodobenzenes, although the rates of methoxydechlorination of the corresponding polychlorobenzenes suggest that in some cases this might occur.Evidence rejecting the possible SRN1 mechanism and supporting nucleophilic attack by a carbanionic species upon iodine is presented.
