- Mechanochemical-Cascaded C-N Cross-Coupling and Halogenation Using N-Bromo- And N-Chlorosuccinimide as Bifunctional Reagents
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Exploration of alternative energy sources for chemical transformations has gained significant interest from chemists, and mechanochemistry is one of those sources. Herein, we report the use of N-bromosuccinimides (NBS) and N-chlorosuccinimides (NCS) as bifunctional reagents for a cascaded C-N bond formation and subsequent halogenation reactions. Under the solvent-free mechanochemical (ball-milling) conditions, the synthesis of a wide range of phenanthridinone derivatives from N-methoxy-[1,1′-biphenyl]-2-carboxamides is accomplished. During the reactions, NBS and NCS first assisted the oxidative C-N coupling reaction and subsequently promoted a halogenation reaction. Thus, the role of NBS and NCS was established to be bifunctional. Overall, a mild, solvent-free, convenient, one-pot, and direct synthesis of various bromo- and chloro-substituted phenanthridinone derivatives was achieved.
- Bera, Shyamal Kanti,Mal, Prasenjit
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p. 14144 - 14159
(2021/09/13)
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- Facile preparation of 3,4-benzocoumarins from 2-arylbenzoic acids with NCS and NAI
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– Treatment of 2-arylbenzoic acids with N-chlorosuccinimide (NCS) and NaI at 70 °C under fluorescent lighting condition gave the corresponding 3,4-benzocoumarins in good yields under transition-metal-free condition. It was found that the reactivity of NCS
- Nakamura, Momoko,Togo, Hideo
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- General and practical carboxyl-group-directed remote C-H oxygenation reactions of arenes
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Two methods for remote aromatic C-H oxygenation reactions, have been developed. Method1, the Cu-catalyzed oxygenation reaction, is highly efficient for cyclization of electron-neutral and electron-rich biaryl carboxylic acids into 3,4-benzocoumarins. Method2, the K2S2O 8-mediated oxygenation reaction, is more general and practical for cyclization of substrates with electron-donating and -withdrawing groups (see scheme). Copyright
- Wang, Yang,Gulevich, Anton V.,Gevorgyan, Vladimir
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p. 15836 - 15840
(2014/04/03)
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- A practical preparation of 2-carboxyphenylboronic acid and its application for the preparation of biaryl-2-carboxylic acids using Suzuki coupling reactions
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A practical synthesis of 2-carboxyphenylboronic from 2-tolylboronic acid and aqueous potassium permanganate under mild conditions is reported. The title compound couples with aryl bromides containing electron-withdrawing groups to give biaryl-2-carboxylic
- Tao, Bin,Goel, Subhash C.,Singh, Jagvir,Boykin, David W.
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p. 1043 - 1046
(2007/10/03)
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