55712-59-9Relevant academic research and scientific papers
Ag(I)-C-H Activation Enables Near-Room-Temperature Direct α-Arylation of Benzo[ b]thiophenes
Colletto, Chiara,Panigrahi, Adyasha,Fernández-Casado, Jaime,Larrosa, Igor
supporting information, p. 9638 - 9643 (2018/07/21)
The first example of near-room-temperature α-arylation of benzo[b]thiophenes is reported. The discovery rests on the observation of a switch in α-/β-regioselectivity at different loadings of Pd2(dba)3·CHCl3 in the coupling between benzo[b]thiophene and 4-iodotoluene. We show that this unprecedented regioselectivity switch is driven by a Ag(I)-mediated C-H activation at the α-C-H position, which becomes the dominant mode of reactivity at low concentrations of Pd. Competition experiments, kinetic studies, KIE, and D/H scrambling experiments have been carried out supporting this mechanism.
Room-Temperature Direct β-Arylation of Thiophenes and Benzo[b]thiophenes and Kinetic Evidence for a Heck-type Pathway
Colletto, Chiara,Islam, Saidul,Juliá-Hernández, Francisco,Larrosa, Igor
supporting information, p. 1677 - 1683 (2016/02/20)
The first example of a regioselective β-arylation of benzo[b]thiophenes and thiophenes at room temperature with aryl iodides as coupling partners is reported. This methodology stands out for its operational simplicity: no prefunctionalization of either st
Completely regioselective direct C-H functionalization of benzo[b]thiophenes using a simple heterogeneous catalyst
Tang, Dan-Tam D.,Collins, Karl D.,Glorius, Frank
supporting information, p. 7450 - 7453 (2013/06/27)
The first completely selective C3 C-H arylation of benzo[b]thiophenes is reported, demonstrating previously unexploited reactivity of palladium. Benzo[b]thiophenes are coupled with readily available aryl chlorides using a ligand-free, dual catalytic system of heterogeneous Pd/C and CuCl. The reaction is operationally simple and insensitive to air and moisture, and it provides valuable products with complete selectivity. Significant investigations into the nature of the active catalytic species and mechanistic considerations are discussed.
Selective palladium-catalysed ipso arylation of α,α- disubstituted benzo[b]thien-2-ylmethanols with aryl bromides using PCy 3 as ligand
Biro, A. Beatrix,Kotschy, Andras
, p. 1364 - 1368 (2008/09/18)
α,α-Diphenylbenzo[b]thien-2-ylmethanol was treated with a series of aryl bromides in the presence of palladium(II) acetate and tricyclohexylphosphane to give the appropriate 2-aryl-benzo[b]thiophenes in good to excellent yield with concomitant formation o
PHOTOREACTIVITE DE SYSTEMES HEXATRIENIQUES HETEROCYCLIQUES. ARYL-2 ET 3 BENZOTHIOPHENE
Buquet, A.,Couture, A.,Lablache-Combier, A.,Pollet, A.
, p. 75 - 81 (2007/10/02)
The photochemical behavior of several benzothiophenes 1-4 in neutral solutions or in the presence of primary and tertiary amines has been examined.In most cases, the photoformation of adducts or dimers, rather than cyclisation, has been observed.An unu
