1251832-81-1Relevant articles and documents
Engaging 1,7-diynes in a photocatalytic Kharasch-type addition/1,5-(SN′′)-substitution cascade toward β-gem-dihalovinyl carbonyls
Wu, Dan,Hao, Wen-Juan,Rao, Qian,Lu, Yi,Tu, Shu-Jiang,Jiang, Bo
, p. 1911 - 1914 (2021)
A new and general photocatalytic Kharasch-type addition/1,5-(SN′′)-substitution cascade of 1,7-diynes with alkyl halides such as BrCCl3and CBr4was reported for the first time, and used to produce 65 hitherto unreported β-gem-dihalovinyl ketones/aldehydes with moderate to excellent yields in a highly regioselective manner. This reaction tolerates a wide scope of substrates, which offers a green and efficient entry to fabricate synthetically important β-gem-dihalovinyl carbonyl scaffolds. Notably, the late-stage application of these resulting β-gem-dihalovinyl carbonyls shows high and unique reactivity profiles and demonstrates the versatility of their derivatization.
Facile preparation of 3-aryl-4-iodoisoquinolines from N-(o-Arylethynyl)benzyl p-toluenesulfonamides with iodine and base
Naruto, Hiroki,Togo, Hideo
, (2021/02/20)
Treatment of N-(o-arylethynyl)benzyl p-toluenesulfonamides with molecular iodine in the presence of NaHCO3 at 60 °C, followed by the reaction with tBuOK at room temperature gave 3-aryl-4-iodoisoquinolines in good yields. 4-Iodo-3-phenylisoquinoline, which is one of the obtained 3-aryl-4-iodoisoquinolines, was further transformed into isoquinoline derivatives smoothly. The present approach is a novel one-pot method for the preparation of 3-aryl-4-iodoisoquinolines from N-(o-arylethynyl)benzyl p-toluenesulfonamides under transition-metal-free conditions.
Modular synthesis of 3-substituted isocoumarinsviasilver-catalyzed aerobic oxidation/6-endoheterocyclization ofortho-alkynylbenzaldehydes
Wu, Hao,Wang, Yi-Chun,Shatskiy, Andrey,Li, Qiu-Yan,Liu, Jian-Quan,K?rk?s, Markus D.,Wang, Xiang-Shan
, p. 6657 - 6664 (2021/08/16)
A method involving silver-catalyzed aerobic oxidation/6-endoheterocyclization ofortho-alkynylbenzaldehydes to yield 3-substituted isocoumarins is described. The developed protocol allows convenient access to a range of synthetically useful 3-substituted isocoumarins and related fused heterocyclolactones in good to high yields, using silver tetrafluoroborate as the catalyst, and atmospheric oxygen as the terminal oxidant and the source of endocyclic oxygen. Mechanistic studies suggest the involvement of a free-radical pathway.