- Benzophenothiazine and Its Cr(III)-Catalyzed Cross Dehydrogenative Couplings
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In stark contrast to phenothiazines and their prevalence for cross-dehydrogenative amination reactions, benzophenothiazine has a pronounced preference for cross-dehydrogenative C-C bond-forming reactions. Moreover, the substrate is very versatile, leading to several new classes of C-C bond-forming reactions and many new oxidative coupling product architectures, including unprecedented indole fused paddlewheel-like structures.
- Bub, Christina L.,Th?nni?en, Vinzenz,Patureau, Frederic W.
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- Phenyl Benzo[b]phenothiazine as a Visible Light Photoredox Catalyst for Metal-Free Atom Transfer Radical Polymerization
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This paper reports use of phenyl benzo[b]phenothiazine (Ph-benzoPTZ) as a visible light-induced metal-free atom transfer radical polymerization (ATRP) photoredox catalyst. Well-controlled polymerizations of various methacrylate monomers were conducted und
- Dadashi-Silab, Sajjad,Pan, Xiangcheng,Matyjaszewski, Krzysztof
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- N -Arylbenzo[ b ]phenothiazines as Reducing Photoredox Catalysts for Nucleophilic Additions of Alcohols to Styrenes: Shift towards Visible Light
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N -Phenylphenothiazines are an important class of photoredox catalysts because they are synthetically well accessible, they allow the tuning of the optoelectronic properties by different substituents, and they have strong reduction properties for activation of alkenes. One of the major disadvantages of N -phenylphenothiazines, however, is the excitation at 365 nm in the UV-A light range. We synthesized three differently dialkylamino-substituted N -phenylbenzo[ b ]phenothiazines as alternative photoredox catalysts and applied them for the nucleo philic addition of alkohols to α-methyl styrene. The additional benzene ring shift the absorbance bathochromically and allows performing the photocatalyses by excitation at 385 nm and 405 nm. This type of photoredox catalysis tolerates other functional groups, as representatively shown for alcohols as substrates with C-C and C-N triple bonds.
- Seyfert, Fabienne,Wagenknecht, Hans-Achim
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supporting information
p. 582 - 586
(2021/01/25)
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- Synthesis of diverse phenothiazines by direct thioamination of arynes with S-(o-bromoaryl)-S-methylsulfilimines and subsequent intramolecular BuchwaldHartwig amination
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A facile method for the synthesis of diverse phenothiazines has been achieved by direct thioamination of aryne intermediates with S-(o-bromoaryl)-S-methylsulfilimines and subsequent intramolecular BuchwaldHartwig amination. Since various sulfilimines could be prepared easily by odorless copper-catalyzed ipso-thiolation of readily available o-bromoarylboronic acids followed by imination and hydrolysis, this approach enables the synthesis of a wide variety of multisubstituted phenothiazines.
- Matsuzawa, Tsubasa,Uchida, Keisuke,Yoshida, Suguru,Hosoya, Takamitsu
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p. 825 - 828
(2018/07/05)
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- Mechanism of Photoinduced Metal-Free Atom Transfer Radical Polymerization: Experimental and Computational Studies
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Photoinduced metal-free atom transfer radical polymerization (ATRP) of methyl methacrylate was investigated using several phenothiazine derivatives and other related compounds as photoredox catalysts. The experiments show that all selected catalysts can b
- Pan, Xiangcheng,Fang, Cheng,Fantin, Marco,Malhotra, Nikhil,So, Woong Young,Peteanu, Linda A.,Isse, Abdirisak A.,Gennaro, Armando,Liu, Peng,Matyjaszewski, Krzysztof
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supporting information
p. 2411 - 2425
(2016/03/05)
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