- Visible Light Induced Aerobic Coupling of Arylboronic Acids Promoted by Hydrazone
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A visible-light-induced oxidative coupling of arylboronic acids has been developed for the synthesis of biaryls. The reaction that employs polydentate hydrazones as the bifunctional catalyst works smoothly under room temperature. It is compatible with a w
- Xia, Hongyu,Wang, Ganghu,Zhao, Dongbo,Zhu, Chunyin
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supporting information
p. 922 - 929
(2022/02/10)
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- Iron-mediated direct arylation of unactivated arenes in air
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Biaryls are a common motif in both natural and synthetic chemicals. Several methods have recently been reported for the preparation of these compounds using direct arylation catalyzed by iron, other base metals, or transition-metal-free systems. To date, these methods have all required inert and/or forcing conditions, which limited their application in routine organic synthesis. In this article we report a protocol for direct arylation using a convenient FeCl3/1,10-phenanthroline system as precatalyst. The reaction proceeds under mild conditions (100 °C), under air, and with non-distilled solvent. A simple, environmentally benign catalytic system based on iron trichloride and phenanthroline has been developed for the direct arylation of unactivated arenes with aryl halides under air. Copyright
- Huang, Yuxing,Moret, Marc-Etienne,Klein Gebbink, Robertus J. M.
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supporting information
p. 3788 - 3793
(2014/06/24)
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- Direct C-H arylations of unactivated arenes catalyzed by amido-functionalized imidazolium salts
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The synthesis of biaryls from unactivated arenes and a broad range of aryl bromides and chlorides via the direct C-H functionalization can be efficiently performed with the aid of amido-functionalized imidazolium salts as organocatalysts. This method avoids the use of toxic transition metal catalysts and organometallic reagents.
- Ghosh, Debalina,Lee, Jhen-Yi,Liu, Chian-Yu,Chiang, Yen-Hsin,Lee, Hon Man
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supporting information
p. 406 - 410
(2014/05/20)
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- p-toluenesulfonohydrazide as highly efficient initiator for direct C-H arylation of unactivated arenes
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p-Toluenesulfonohydrazide (PTSH) was shown to promote the highly efficient direct arylation of unactivated arenes with aryl iodides, bromides, or chlorides in the presence of potassium tert-butoxide without the assistance of any transition metals. The reaction proceeds through base-promoted homolytic aromatic substitution (BHAS) involving aryl radicals and arylradical anions as intermediates. (Chemical Equation Presented).
- Song, Qiao,Zhang, Dongmei,Zhu, Qihua,Xu, Yungen
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supporting information
p. 5272 - 5274
(2015/02/05)
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- Simple alcohols promoted direct C-H arylation of unactivated arenes with aryl halides
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Simple and cheap alcohols can promote the direct arylation of unactivated arenes with aryl iodides and bromides in the presence of potassium tert-butoxide. This transition-metal-free aromatic C-H transformation offers a cheap and easy practical way to synthesize biaryls under mild conditions. The Royal Society of Chemistry.
- Liu, Wei,Tian, Fei,Wang, Xiaolei,Yu, Hao,Bi, Yanlan
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p. 2983 - 2985
(2013/05/21)
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- Phenyl hydrazine as initiator for direct arene C-H arylation via base promoted homolytic aromatic substitution
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A simple and efficient direct radical arylation of unactivated arenes is described which uses cheap and commercially available phenyl hydrazine as an initiator. The reaction occurs through a base promoted homolytic aromatic substitution (BHAS) mechanism involving aryl radicals and aryl radical anions as intermediates and offers a practical approach for preparation of an array of substituted biaryls.
- Dewanji, Abhishek,Murarka, Sandip,Curran, Dennis P.,Studer, Armido
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supporting information
p. 6102 - 6105
(2014/01/06)
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- C-H arylation of unactivated arenes with aryl halides catalyzed by cobalt porphyrin
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A general procedure for cobalt-catalyzed direct C-H arylation of unactivated arenes has been discovered. This method employs aryl halides as the direct coupling partners with arenes without using any Grignard-type reagents. This catalysis opens a new methodology for the preparation of symmetrical as well as unsymmetrical biaryls in a user-friendly approach.
- To, Ching Tat,Chan, Tek Long,Li, Bao Zhu,Hui, Ying Ying,Kwok, Tsz Yiu,Lam, Suet Yu,Chan, Kin Shing
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supporting information; experimental part
p. 1023 - 1026
(2011/03/20)
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- Direct arylation of unactivated aromatic C-H bonds catalyzed by a stable organic radical
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A stable zwitterionic radical can catalyze direct arylation of unactivated aromatic C-H bonds via a chain homolytic aromatic substitution mechanism in the presence of potassium tert-butoxide.
- Yong, Guo-Ping,She, Wen-Long,Zhang, Yi-Man,Li, Ying-Zhou
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supporting information; experimental part
p. 11766 - 11768
(2011/11/29)
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- Tert-butoxide-mediated arylation of benzene with aryl halides in the presence of a catalytic 1,10-phenanthroline derivative
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Sodium tert-butoxide mediates the coupling of aryl halides with benzene derivatives without the aid of transition metal catalysts but with a catalytic 1,10-phenanthroline derivative.
- Shirakawa, Eiji,Itoh, Ken-Ichi,Higashino, Tomohiro,Hayashi, Tamio
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supporting information; experimental part
p. 15537 - 15539
(2010/12/30)
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- Structure-reactivity relationships in negishi cross-coupling reactions
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Competition experiments have been performed to determine the relative reactivities of substituted bromobenzenes and of different arylzinc reagents in the [Pd(PPh3)4]-catalyzed Negishi cross-coupling reaction in THF at 25 °C. The crosscoupling reactions are accelerated by electron acceptors in the bromobenzenes, the effect of which increases in the order ortho a larger effect than substituent variations in the arylzinc halides (ρ = -0.98).
- Dong, Zhi-Bing,Manolikakes, Georg,Shi, Lei,Knochel, Paul,Mayr, Herbert
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supporting information; experimental part
p. 248 - 253
(2010/03/30)
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