- THE FIRST APPLICATION OF ANION-CATALYZED PHASE-TRANSFER CATALYSIS TO FRIEDEL-CRAFTS ALKYLATION
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Friedel-Crafts alkylation proceeded by catalysis of tetrakisborate (TFPB) in a dichloromethane-aqueous sulfuric acid two-phase system.Kinetic evidence indicated that oxonium-TFPB ion-pair in the organic phase was operative as a catalyst.
- Kobayashi, Hiroshi,Sonoda, Takaaki,Iwamoto, Hidetoshi
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- Electrochemical Activation of Diverse Conventional Photoredox Catalysts Induces Potent Photoreductant Activity**
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Herein, we disclose that electrochemical stimulation induces new photocatalytic activity from a range of structurally diverse conventional photocatalysts. These studies uncover a new electron-primed photoredox catalyst capable of promoting the reductive cleavage of strong C(sp2)?N and C(sp2)?O bonds. We illustrate several examples of the synthetic utility of these deeply reducing but otherwise safe and mild catalytic conditions. Finally, we employ electrochemical current measurements to perform a reaction progress kinetic analysis. This technique reveals that the improved activity of this new system is a consequence of an enhanced catalyst stability profile.
- Chernowsky, Colleen P.,Chmiel, Alyah F.,Wickens, Zachary K.
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supporting information
p. 21418 - 21425
(2021/08/25)
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- Phosphorous acid-catalyzed alkylation of phenols with alkenes
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A H3PO3-catalyzed alkylation of phenols with alkenes is achieved in a facile, efficient, and selective manner. The reaction shows a unique selectivity, i.e., excellent regioselectivity, thorough suppression of overalkylation, without alkylation of a simple phenyl ring, and can selectively provide ortho-, meta-, or para-alkylated phenol derivatives in good to excellent yields. This feature along with mild reaction conditions, sensitive functional group tolerance, and scale-up synthesis and late modification of phenolic bioactive compounds make it an ideal and practical alternative for the modification of phenols.
- Wu, Shaofeng,Dong, Jianyu,Zhou, Dan,Wang, Wan,Liu, Long,Zhou, Yongbo
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p. 14307 - 14314
(2020/01/31)
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- Hydroarylation of alkynes and alkenes through alumina-sulfuric acid catalyzed regioselective C–C bond formation
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A highly atom-efficient synthetic protocol for hydroarylation of terminal-aryl alkynes and styrene through the regioselective C–C bond formation via the electrophilic addition of naphthols and substituted phenols has been developed using alumina-sulfuric acid as a heterogeneous supported solid acid catalyst. This methodology shows excellent regioselectivity and affords the desired product in good to excellent yield. The heterogeneous catalyst can also be recycled efficiently without much loss of activity.
- Pramanik, Amit,Ghatak, Avishek,Khan, Sagar,Bhar, Sanjay
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supporting information
p. 1091 - 1095
(2019/03/26)
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- Room Temperature Catalyst System for the Hydroarylation of Olefins
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A simple protocol for the hydroarylation of olefins to yield diarylmethine products is described. A Friedel-Crafts-type synthetic strategy allows direct access to biorelevant products in high atom efficiency. A combination of substoichiometric amounts of TMSCl and ZnBr2 promotes a rapid hydroarylation process at ambient temperature. The method is high yielding and is amenable to scale-up protocols.
- Lee, Siu Yin,Villani-Gale, Alexander,Eichman, Chad C.
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supporting information
p. 5034 - 5037
(2016/10/14)
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- BENZYLPHENOL DERIVATIVES AS ANTIOXIDANTS FOR AUTOXIDATION OF TETRALIN.
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A series of 4-benzylphenols, 2-methyl-4-benzylphenols, 4-methyl-2-benzylphenols and 4-methoxy-2-benzylphenols have been prepared and evaluated as antioxidants for tetralin at 60 degree C by means of an oxygen-absorption method. Very good activities have been observed with a series of 4-methoxy-2-benzylphenols. The electrochemical oxidation potentials of these compounds were determined using linear-sweep voltammetry. The antioxidative activities were found to correlate with both the **1**3C NMR chemical shifts ( delta ) of the ipsocarbon of the OH substituents and their peak potentials (E//p).
- Yamada,Nishiyama,Suzuura,Yamamura
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p. 115 - 119
(2007/10/02)
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