- Direct C(sp3)–H Sulfonylation of Xanthene Derivatives with Sodium Sulfinates by Oxidative Copper Catalysis
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By employing a readily available CuCl/DDQ catalyst system, we herein report a direct C(sp3)–H sulfonylation of xanthene derivates with odorless sodium sulfinates. Various 9H-xanthenes, thioxanthenes, and 9,10-dihydroacridines are efficiently transformed into the desired benzylic sulfonyl products via a radical/radical cross-coupling process, proceeding with the merits of broad substrate scope, operational simplicity, good functional group compatibility, and mild reaction conditions.
- Jiang, Huanfeng,Song, Qinghao,Sun, Yanping,Zhang, Min,Zhao, He
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p. 371 - 377
(2021/12/24)
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- Acid-catalyzed oxidative cross-coupling of acridans with silyl diazoenolates and a Rh-catalyzed rearrangement: two-step synthesis of γ-(9-acridanylidene)-β-keto esters
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A MsOH-catalyzed oxidative cross-coupling of acridans and silyl diazoenolates and a Rh2(OAc)4-catalyzed rearrangement of the resultant diazo products are described. The reactions provide various γ-(9-acridanylidene)-β-keto esters in good yields, which bear an active α-methylene unit for further functionalization.
- Li, Weiyu,Xu, Hao,Zhou, Lei
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p. 5649 - 5657
(2021/07/02)
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- Oxidative C-H bond functionalization and ring expansion with TMSCHN2: A copper(I)-catalyzed approach to dibenzoxepines and dibenzoazepines
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Tricyclic dibenzoxepines and dibenzazepines are important therapeutic agents for the pharmaceutical industry and academic research. However, their syntheses are generally rather tedious, requiring several steps that involve a Wagner-Meerwein-type rearrangement under harsh conditions. Herein, we present the first copper(I)-catalyzed oxidative C-H bond functionalization and ring expansion with TMSCHN2 to yield these important derivatives in a facile and straightforward way. Cut a long story short: Tricyclic dibenzoxepines and dibenzazepines are important therapeutic agents for pharmaceuticals, but their syntheses are generally rather tedious. A copper(I)-catalyzed oxidative C-H bond functionalization and ring expansion sequence with TMSCHN2 has been developed to yield these important derivatives in a facile and straightforward way.
- Stopka, Tobias,Marzo, Leyre,Zurro, Mercedes,Janich, Simon,Würthwein, Ernst-Ulrich,Daniliuc, Constantin G.,Alemán, José,Manche?o, Olga García
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p. 5049 - 5053
(2015/04/27)
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- Metal-free TEMPO-catalyzed oxidative C-C bond formation from Csp 3-H bonds using molecular oxygen as the oxidant
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An efficient TEMPO-catalyzed oxidative C-C bond formation with two Csp 3-H bonds using molecular oxygen as the oxidant has been developed. The novel transformation provides a new strategy for the TEMPO-O2 catalysis to construct C-C bonds. The advantages of this method include: (1) relatively mild and neutral conditions; (2) simplicity and safety of operation; (3) a stoichiometric amount of dangerous oxidants, any transition metals, additives, even solvent, is not required.
- Zhang, Bo,Cui, Yuxin,Jiao, Ning
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scheme or table
p. 4498 - 4500
(2012/06/01)
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- Autoxidative carbon-carbon bond formation from carbonhydrogen bonds
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(Figure Presented) Only oxygen and acid! The oxidative coupling of xanthene and other activated benzylic compounds with carbon nucleophiles such as ketones, can be performed under ambient conditions without solvent by simply using oxygen and catalytic amounts of methanesulfonic acid. The proposed reaction mechanism involves substrate activation by formation of hydroperoxides; the method can therefore be regarded as an "autoxidative coupling reaction".
- Pinter, Aron,Sud, Abhishek,Sureshkumar, Devarajulu,Klussmann, Martin
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supporting information; experimental part
p. 5004 - 5007
(2010/09/08)
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- Nonconventional Friedel-Crafts chemistry: Part V - Cyclization of triphenylamine under alkylative and arylative conditions to phenylcarbazole and acridan derivatives
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Triphenylamine reacts with aluminium chloride in bezene, carbon disulphide and dichloromethane to give 9-phenylcarbazole.It also reacts with other alkylating agents such as diphenylmethyl chloride or diphenylmethanol to yield acridan derivatives.A mechanism has been suggested that rationalizes the ortho-alkylation and cyclization of triphenylamine under Friedel-Crafts reaction conditions.
- El-Zohry, Maher F.
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p. 275 - 280
(2007/10/02)
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