50551-29-6Relevant articles and documents
Investigation of Straightforward, Photoinduced Alkylations of Electron-Rich Heterocompounds with Electron-Deficient Alkyl Bromides in the Sole Presence of 2,6-Lutidine
Fuks, Elina,Huber, Laura,Schinkel, Thea,Trapp, Oliver
supporting information, p. 6192 - 6198 (2020/08/19)
Alkylations of simple electron-rich heterocompounds deliver valuable target structures in bioorganic and medicinal chemistry. Herein, we present a straightforward and photosensitizer free approach for the photoinduced C–C coupling of electron-rich unsaturated heterocompounds with alkyl bromides using 405 nm and 365 nm irradiation. Comprehensive mechanistic studies indicate the involvement of 2,6-lutidine in the formation of a non-covalently bound intermediate to which the function of a photosensitizer is attributed. UV/Vis spectra reveal the formation of a bathochromic shifted band when the electron-deficient alkyl bromide is mixed with the structural motif of 2,6-substituted pyridine. Upon photochemical excitation of this band, we find the initiation of the C–C bond-forming reaction. Using this approach highly versatile alkylation products, e.g. α-substituted ketones and 2-substituted furan, thiophene, and pyrrole derivatives, are obtained in high selectivity. Furthermore, this synthetic methodology can be applied to access substituted indoles, which cannot be obtained by other transformations.
Visible light/Ir(III) photocatalytic initiation of xanthate-based radical-chain reactions: Xanthate group transfer and oxidative addition to aromatic systems
López-Mendoza, Pedro,Díaz, John E.,Loaiza, Alix E.,Miranda, Luis D.
supporting information, p. 5494 - 5502 (2018/05/16)
A photocatalyzed redox generation of radicals from O-ethyl xanthates to generate electrophilic radicals under photoredox catalysis, using Ir(ppy)3 and blue LEDs irradiation is described. The protocol can be used in classical xanthate-based inter- and intra-molecular group transfer reactions and oxidative radical addition to several heteroaromatic systems. The process does not require high temperature and reactions are cleaner compared with the traditional peroxide initiation. In the oxidative addition to aromatic systems, the oxidation process is part of the catalytic cycle and does not require a stoichiometric oxidant such as DLP which is particularly difficult to separate from the product.
1-and 2-azafulvenes
Barcock,Moorcroft,Storr,Young,Fuller
, p. 1187 - 1190 (2007/10/02)
Flash pyrolysis of dialkylaminopyrroles and thermolysis of 2-pyrrylmethyl phenyl sulfoxide at 65°C in solution gave azafulvenes which were trapped with a variety of nucleophiles.
