Radical-radical cross coupling reactions of photo-excited fluorenones.
نویسندگان
چکیده
Radical-radical cross coupling reactions of photoexcited 9-fluorenones have been accomplished for the first time, leading to the synthesis of 9-alkyl, pyrollidinyl and spiro-THF derivatives of 9-fluorenones. The method also reveals, for the first time, the behaviour of ketyl radicals in decarboxyaltive alkylation and ring expansion reactions.
منابع مشابه
Metal free TBHP-promoted intramolecular carbonylation of arenes via radical cross-dehydrogenative coupling: synthesis of indenoquinolinones, 4-azafluorenones and fluorenones.
A metal-free, TBHP-promoted economical route is developed via the sp(2) C-H bond functionalization strategy for the synthesis of indenoquinolinones, 4-azafluorenones and fluorenones. Reactions provided excellent yield of the products under mild conditions. We have successfully synthesized 11H-indeno[1,2-b]quinolin-11-one, an antibacterial agent, in excellent yields.
متن کاملPhotoinduced C-Br homolysis of 2-bromobenzophenones and Pschorr ring closure of 2-aroylaryl radicals to fluorenones.
A variety of diversely substituted 2-aroylaryl radicals, generated by photoinduced homolysis of 2-bromoarylketones, is shown to undergo Pschorr cyclization to yield fluorenones in moderate to excellent yields. The photochemical results illustrate that the substituents in the two phenyl rings of the 2-bromobenzophenone skeleton exert a dramatic influence on the reactivity of the derived 2-aroyla...
متن کاملStabilization of Two Radicals with One Metal: A Stepwise Coupling Model for Copper-Catalyzed Radical–Radical Cross-Coupling
Transition metal-catalyzed radical-radical cross-coupling reactions provide innovative methods for C-C and C-heteroatom bond construction. A theoretical study was performed to reveal the mechanism and selectivity of the copper-catalyzed C-N radical-radical cross-coupling reaction. The concerted coupling pathway, in which a C-N bond is formed through the direct nucleophilic addition of a carbon ...
متن کاملControl of Photo-electron-transfer Induced Radical Production by Micellar Cages, Heavy-atom Substituents and Magnetic Fields
Intramicellar radical pair formation and recombination kinetics in the electron transfer quenching of the thionine triplet by aniline and various monohalogenated anilines have been studied by microsecond and nanosecond laser flash spectroscopy in reversed micellar solution of COBA in benzene. Clear kinetic evidence of the micellar cage effect is provided by a comparative spectro-kinetical study...
متن کاملReaction cavities of liquid and solid phases of a long n-alkane, n-nonadecane, as probed by the regio- and stereo-chemical fates of two singlet radical pairs.
The regio- and stereo-chemistries of photo-Fries reactions of 1-naphthyl (R)-2-phenylpropanoate ((R)-1) and photo-Claisen reactions of 1-naphthyl (R)-1-phenylethyl ether ((R)-2) have been investigated in the liquid and solid phases of n-nonadecane. The results are compared with those obtained in a lower and higher viscosity liquid n-alkane. Irradiation of (R)-1 yields a prochiral singlet 1-naph...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Organic & biomolecular chemistry
دوره 14 40 شماره
صفحات -
تاریخ انتشار 2016