24423-07-2Relevant academic research and scientific papers
Visible Light Induced Aerobic Coupling of Arylboronic Acids Promoted by Hydrazone
Xia, Hongyu,Wang, Ganghu,Zhao, Dongbo,Zhu, Chunyin
supporting information, p. 922 - 929 (2022/02/10)
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
Direct C-H arylations of unactivated arenes catalyzed by amido-functionalized imidazolium salts
Ghosh, Debalina,Lee, Jhen-Yi,Liu, Chian-Yu,Chiang, Yen-Hsin,Lee, Hon Man
supporting information, p. 406 - 410 (2014/05/20)
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.
p-toluenesulfonohydrazide as highly efficient initiator for direct C-H arylation of unactivated arenes
Song, Qiao,Zhang, Dongmei,Zhu, Qihua,Xu, Yungen
supporting information, p. 5272 - 5274 (2015/02/05)
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).
Iron-mediated direct arylation of unactivated arenes in air
Huang, Yuxing,Moret, Marc-Etienne,Klein Gebbink, Robertus J. M.
supporting information, p. 3788 - 3793 (2014/06/24)
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
Simple alcohols promoted direct C-H arylation of unactivated arenes with aryl halides
Liu, Wei,Tian, Fei,Wang, Xiaolei,Yu, Hao,Bi, Yanlan
, p. 2983 - 2985 (2013/05/21)
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.
Phenyl hydrazine as initiator for direct arene C-H arylation via base promoted homolytic aromatic substitution
Dewanji, Abhishek,Murarka, Sandip,Curran, Dennis P.,Studer, Armido
supporting information, p. 6102 - 6105 (2014/01/06)
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.
C-H arylation of unactivated arenes with aryl halides catalyzed by cobalt porphyrin
To, Ching Tat,Chan, Tek Long,Li, Bao Zhu,Hui, Ying Ying,Kwok, Tsz Yiu,Lam, Suet Yu,Chan, Kin Shing
supporting information; experimental part, p. 1023 - 1026 (2011/03/20)
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.
Direct arylation of unactivated aromatic C-H bonds catalyzed by a stable organic radical
Yong, Guo-Ping,She, Wen-Long,Zhang, Yi-Man,Li, Ying-Zhou
supporting information; experimental part, p. 11766 - 11768 (2011/11/29)
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.
Tert-butoxide-mediated arylation of benzene with aryl halides in the presence of a catalytic 1,10-phenanthroline derivative
Shirakawa, Eiji,Itoh, Ken-Ichi,Higashino, Tomohiro,Hayashi, Tamio
supporting information; experimental part, p. 15537 - 15539 (2010/12/30)
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.
Structure-reactivity relationships in negishi cross-coupling reactions
Dong, Zhi-Bing,Manolikakes, Georg,Shi, Lei,Knochel, Paul,Mayr, Herbert
supporting information; experimental part, p. 248 - 253 (2010/03/30)
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).
