147619-68-9Relevant academic research and scientific papers
Nickel-Catalyzed Asymmetric Hydrogenation of Cyclic Alkenyl Sulfones, Benzo[ b]thiophene 1,1-Dioxides, with Mechanistic Studies
Liu, Gongyi,Tian, Kui,Li, Chenzong,You, Cai,Tan, Xuefeng,Zhang, Heng,Zhang, Xumu,Dong, Xiu-Qin
supporting information, p. 668 - 675 (2021/02/06)
A highly efficient catalytic system based on the cheap transition metal nickel for the asymmetric hydrogenation of challenging cyclic alkenyl sulfones, 3-substituted benzo[b]thiophene 1,1-dioxides, was first successfully developed. A series of hydrogenation products, chiral 2,3-dihydrobenzo[b]thiophene 1,1-dioxides, were obtained in high yields (95-99%) with excellent enantioselectivities (90-99% ee). According to the results of nonlinear effect studies, deuterium-labeling experiments, and DFT calculation investigations, a reasonable catalytic mechanism for this nickel-catalyzed asymmetric hydrogenation was provided, which displayed that the two added hydrogen atoms of the hydrogenation products could be from H2 through the insertion of Ni-H and subsequent hydrogenolysis.
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.
Continuous-Flow Synthesis of Biaryls by Negishi Cross-Coupling of Fluoro- and Trifluoromethyl-Substituted (Hetero)arenes
Roesner, Stefan,Buchwald, Stephen L.
supporting information, p. 10463 - 10467 (2016/08/24)
A continuous-flow method for the regioselective arylation of fluoroarenes and fluoropyridines has been developed. The telescoped procedure reported here consists of a three-step metalation, zincation, and Negishi cross-coupling sequence, providing efficient access to a variety of functionalized 2-fluorobiaryl products. Precise temperature control of the metalation step, made possible by continuous-flow technology, allowed for the efficient preparation of the arylated products in high yields and short residence times. Additionally, several examples of the regioselective arylation of benzotrifluoride derivatives are also provided.
A new and practical grignard-coupling-fluorination sequence: Synthesis of 2-aryl fluoroarenes
Anbarasan, Pazhamalai,Neumann, Helfried,Beller, Matthias
supporting information; experimental part, p. 1775 - 1778 (2011/03/19)
A new strategy for the synthesis of 2-aryl-and 2-heteroaryl fluoroarenes has been developed. An intermolecular domino Grignard-coupling-fluorination sequence affords a range of 2-fluorobiaryls from aryl bromides under mild conditions. This methodology can be further extended to the synthesis of 2′-aryl-2-fluorobiphenyls.
