18138-77-7Relevant articles and documents
Synthesis of styryl tetrahydrofurans and tetrahydropyrans via addition of radicals to unsaturated sulfimides
Clark, Andrew J.,Rooke, Stuart,Sparey, Tim J.,Taylor, Paul C.
, p. 909 - 912 (1996)
The addition of tetrahydrofuranyl or tetrahydropyranyl radicals to (E)-styryl sulfimide derivatives furnishes the corresponding (E)-styryl tetrahydrofurans or tetrahydropyrans respectively. The corresponding radical reactions with (Z)-styryl sulfimides gives rise to a mixture of (E) and (Z) isomers, this is in contrast to the Et3B mediated reaction, which is stereoselective.
Phenylglyoxylic Acid: An Efficient Initiator for the Photochemical Hydrogen Atom Transfer C?H Functionalization of Heterocycles
Papadopoulos, Giorgos N.,Kokotou, Maroula G.,Spiliopoulou, Nikoleta,Nikitas, Nikolaos F.,Voutyritsa, Errika,Tzaras, Dimitrios I.,Kaplaneris, Nikolaos,Kokotos, Christoforos G.
, p. 5934 - 5944 (2020/09/09)
C?H functionalization at the α-position of heterocycles has become a rapidly growing area of research. Herein, a cheap and efficient photochemical method was developed for the C?H functionalization of heterocycles. Phenylglyoxylic acid (PhCOCOOH) could behave as an alternative to metal-based catalysts and organic dyes and provided a very general and wide array of photochemical C?H alkylation, alkenylation, and alkynylation, as well as C?N bond forming reaction methodologies. This novel, mild, and metal-free protocol was successfully employed in the functionalization of a wide range of C?H bonds, utilizing not only O- or N-heterocycles, but also the less studied S-heterocycles.
Photoredox Oxo-C(sp3)-H Bond Functionalization via in Situ Cu(I)-Acetylide Catalysis
Song, Zi-Qi,Liu, Zan,Gan, Qi-Chao,Lei, Tao,Tung, Chen-Ho,Wu, Li-Zhu
supporting information, p. 832 - 836 (2020/01/31)
A unified strategy for the synthesis of 2-vinyl heterocycles is reported. With visible light irradiation, simple and cheap CuCl is able to functionalize a terminal alkyne, giving Cu(I)-acetylide in situ. Unlike the case of noble metals or organic dye photocatalysts, this critical Cu(I)-acetylide not only activates the C-H bond of terminal alkynes but also serves as a photocatalyst to achieve varieties of 2-vinyl heterocycles in good to excellent yields, even for large scale and late-stage functionalization of natural product.
