21906-01-4Relevant academic research and scientific papers
Fe(II)-catalyzed amination of aromatic C-H bonds via ring opening of 2 H-azirines: Synthesis of 2,3-disubstituted indoles
Jana, Samaresh,Clements, MacK D.,Sharp, Barry K.,Zheng, Nan
supporting information; experimental part, p. 3736 - 3739 (2010/11/03)
A general method for the synthesis of 2,3-disubstituted indoles is described. The key feature of this method is the amination of aromatic C-H bonds via FeCl2-catalyzed ring opening of 2H-azirines. The method tolerates a variety of functional groups such as Br, F, NO2, OMe, CF3, OTBS, alkenes, and OPiv. The method can also be extended to synthesize azaindoles.
Baeyer-Villiger monooxygenase-catalyzed kinetic resolution of racemic α-alkyl benzyl ketones: enzymatic synthesis of α-alkyl benzylketones and α-alkyl benzylesters
Rodriguez, Cristina,Gonzalo, Gonzalo de,Torres Pazmino, Daniel E.,Fraaije, Marco W.,Gotor, Vicente
experimental part, p. 1168 - 1173 (2009/10/02)
The application of three BVMOs for the enantioselective oxidation of 3-phenylbutan-2-ones with different substituents in the aromatic moiety is described. By choosing the appropriate biocatalyst and substrate combination, chiral ketones and esters can be obtained with excellent enantiopurities. This methodology could also be applied to the resolution of racemic α-alkyl benzylketones with longer alkyl chains as well as with two substituted α-substituted benzylacetones. A kinetic analysis revealed that the BVMOs studied effectively convert all tested compounds showing that the enzymes are tolerant towards the substrate structure while being highly enantioselective. These properties render BVMOs as valuable biocatalysts for the preparation of compounds with high interest in organic synthesis.
Ni-catalyzed mild arylation of α-halocarbonyl compounds with arylboronic acids
Liu, Chao,He, Chuan,Shi, Wei,Chen, Mao,Lei, Aiwen
, p. 5601 - 5604 (2008/09/17)
A simple yet powerful Ni catalyst can be used to promote direct arylations of α-halocarbonyl compounds, including a range of esters, amides, and ketones, with various arylboronic acids under mild conditions. The method tolerates β-hydrogens and functional groups in the substrates and offers reactivity and selectivity profiles that are complementary to those found in the well-established Buchwald-Hartwig approach.
Arenediazonium o-benzenedisulfonimides in Heck-type arylation of allylic alcohols
Barbero, Margherita,Cadamuro, Silvano,Dughera, Stefano
, p. 3443 - 3452 (2008/02/12)
Arenediazonium o-benzenedisulfonimides were reacted with primary and secondary allylic alcohols. The reactions, carried out in aqueous ethanol in the presence of palladium(II) acetate as precatalyst and sodium hydrogen carbonate as base, gave the arylation products with good overall conversion. In all cases, the major products were the β-arylated carbonyl derivatives. The o-benzene-disulfonimide was recovered in high yield from all the reactions, and it was recycled for the preparation of other salts. Georg Thieme Verlag Stuttgart.
