89407-24-9Relevant academic research and scientific papers
Site-Selective C?S Bond Formation at C?Br over C?OTf and C?Cl Enabled by an Air-Stable, Easily Recoverable, and Recyclable Palladium(I) Catalyst
Scattolin, Thomas,Senol, Erdem,Yin, Guoyin,Guo, Qianqian,Schoenebeck, Franziska
supporting information, p. 12425 - 12429 (2018/09/18)
This report widens the repertoire of emerging PdI catalysis to carbon–heteroatom, that is, C?S bond formation. While Pd0-catalyzed protocols may suffer from the formation of poisonous sulfide-bound off-cycle intermediates and lack of selectivity, the mechanistically diverse PdI catalysis concept circumvents these challenges and allows for C?S bond formation (S–aryl and S–alkyl) of a wide range of aryl halides. Site-selective thiolations of C?Br sites in the presence of C?Cl and C?OTf were achieved in a general and a priori predictable fashion. Computational, spectroscopic, X-ray, and reactivity data support dinuclear PdI catalysis to be operative. Contrary to air-sensitive Pd0, the active PdI species was easily recovered in the open atmosphere and subjected to multiple rounds of recycling.
ETUDE DES REACTIONS DE SRN1-PARTIE 10 ACTION DE SULFANIONS SUR LES HALOGENURES D'ARYLE FONCTIONNALISES. SYNTHESE DIRECTE DE BENZOTHIOPHENES ET THIENOPYRIDINES
Beugelmans, Rene,Bois-Choussy, Michele,Boudet, Bernard
, p. 4153 - 4162 (2007/10/02)
Functionalized aromatic halides Ar1XY (Ar1=C6H4, Y=OCH3,CONH2,CN,COCH3,CHO,COC6H5) undergo SRN1 reactions with sulphur anions -SR, either simple (R=C2H5,CH2C6H5) or functionalized (R=(CH2)2OH,(CH2)2CO2Et,CH2CO2Et).Products Ar1YS- formed from the fragmentation of the radical anion Ar1YSR- are related to the redox potential of the aryl moiety Ar1Y and with the energy of the bond S-R.In the heterocyclic series (Ar2=pyridine, Ar3=quinoline) a similar relationship appears but a competitive SN(AR) reaction occurs for pyridine substrates bearing an electron withdrawing group.A direct synthesis of benzothiophen via SRN1 reaction and an improved synthesis of thienopyridines based on the SN(Ar) reaction are reported.
