2720-93-6Relevant articles and documents
Photoredox catalysis using infrared light via triplet fusion upconversion
Ravetz, Benjamin D.,Pun, Andrew B.,Churchill, Emily M.,Congreve, Daniel N.,Rovis, Tomislav,Campos, Luis M.
, p. 343 - 346 (2019)
Recent advances in photoredox catalysis have made it possible to achieve various challenging synthetic transformations, polymerizations and surface modifications1–3. All of these reactions require ultraviolet- or visible-light stimuli; however,
Modular Access to Spiro-dihydroquinolines via Scandium-Catalyzed Dearomative Annulation of Quinolines with Alkynes
Lou, Shao-Jie,Luo, Gen,Yamaguchi, Shigeru,An, Kun,Nishiura, Masayoshi,Hou, Zhaomin
supporting information, p. 20462 - 20471 (2021/12/03)
The catalytic enantioselective construction of three-dimensional molecular architectures from planar aromatics such as quinolines is of great interest and importance from the viewpoint of both organic synthesis and drug discovery, but there still exist many challenges. Here, we report the scandium-catalyzed asymmetric dearomative spiro-annulation of quinolines with alkynes. This protocol offers an efficient and selective route for the synthesis of spiro-dihydroquinoline derivatives containing a quaternary carbon stereocenter with an unprotected N-H group from readily accessible quinolines and diverse alkynes, featuring high yields, high enantioselectivity, 100% atom-efficiency, and broad substrate scope. Experimental and density functional theory studies revealed that the reaction proceeded through the C-H activation of the 2-aryl substituent in a quinoline substrate by a scandium alkyl (or amido) species followed by alkyne insertion into the Sc-aryl bond and the subsequent dearomative 1,2-addition of the resulting scandium alkenyl species to the C=N unit in the quinoline moiety. This work opens a new avenue for the dearomatization of quinolines, leading to efficient and selective construction of spiro molecular architectures that were previously difficult to access by other means.
Ring-Expansion Strategy for α-Aryl Azahelicene Construction: Building Blocks for Optoelectronic Materials
Chao, Zengyin,Feng, Jia,Gu, Zhenhua,Hong, Biqiong,Wang, Limin,Xue, Xiaoping
supporting information, p. 8056 - 8061 (2021/10/25)
An acid-mediated rapid synthesis of α-aryl azahelicenes via C-C bond cleavage of helical 9H-fluoren-9-ols is reported. The newly introduced aryl ring and pyridine moieties provide an excellent opportunity to further tune the properties of azahelicences: i.e., photoluminescence. The novel α-aryl azahelicenes showcase high circularly polarized luminescence (CPL) efficiencies (4.5 × 10-3) as well as CPL brightness (BCPL), reaching 7.39 M-1 cm-1, which indicates a potential application as chiral emitters.
