1259894-87-5Relevant academic research and scientific papers
Visible-Light-Induced Cycloaddition of α-Ketoacylsilanes with Imines: Facile Access to β-Lactams
Ye, Jian-Heng,Bellotti, Peter,Paulisch, Tiffany O.,Daniliuc, Constantin G.,Glorius, Frank
, p. 13671 - 13676 (2021)
We report the synthesis of β-lactams from α-ketoacylsilanes and imines, which proceeds via a formal [2+2] photochemical cycloaddition with in situ generation of siloxyketene. This mild and operationally simple reaction proceeds in an atom-economic fashion with broad substrate scope, including aldimines, ketimines, hydrazones, and fused nitrogen heterocycles, affording a variety of important β-lactams with satisfactory diastereoselectivities in most cases. This reaction also features good functional-group tolerance, facile scalability and product diversification. Experimental and computational studies suggest that α-ketoacylsilanes can serve as photochemical precursors by engaging in a 1,3 silicon shift to the distal carbonyl group.
Photoredox Radical/Polar Crossover Enables Construction of Saturated Nitrogen Heterocycles
Pantaine, Lo?c R.E.,Milligan, John A.,Matsui, Jennifer K.,Kelly, Christopher B.,Molander, Gary A.
supporting information, p. 2317 - 2321 (2019/03/26)
Photoredox-mediated radical/polar crossover (RPC) processes offer new avenues for the synthesis of cyclic molecules. This process has been realized for the construction of medium-sized saturated nitrogen heterocycles. Photocatalytically generated alkyl ra
Novel thiophene-based cycloruthenated compounds: Synthesis, characterization, and reactivity
Cuesta, Luciano,Maluenda, Irene,Soler, Tatiana,Navarro, Rafael,Urriolabeitia, Esteban P.
experimental part, p. 37 - 45 (2011/02/27)
The reactions between a series of thiophene-based imines with [(η6-C6H6)RuCl(μ-Cl)]2, in a basic medium, and in MeCN give a family of ruthenacycles of stoichiometry [Ru(C∧N)(NCMe)4]PF6 (C∧N = orthometalated thiopheneimine). In these species, the C-H activation process is produced in most cases at the thiophene ring. When two C-H bonds are competing (thiophene vs aryl), the cyclometalation can be driven regioselectively to the thiophene unit or to the aryl ring as a function of the location of the iminic C = N bond. Cyclometalation can also be oriented to positions 2 or 3 of the thiophene depending on the situation of the imine in the heterocycle (3 or 2, respectively). In all studied cases, the η6-C6H 6 ligand was substituted by acetonitrile. The X-ray structures of two representative complexes have been determined. These thiophene-based metallacycles react with iodine under very mild conditions affording, after hydrolysis, substituted 3-iodo-2-formyl(benzo)thiophenes or substituted 2-iodo-3-formyl(benzo)thiophenes, as a function of the organometallic precursor.
