1419611-75-8Relevant academic research and scientific papers
Transition-Metal-Free Coupling of 1,3-Dipoles and Boronic Acids as a Sustainable Approach to C?C Bond Formation
Livingstone, Keith,Bertrand, Sophie,Kennedy, Alan R.,Jamieson, Craig
supporting information, p. 10591 - 10597 (2020/07/25)
The need for alternative, complementary approaches to enable C?C bond formation within organic chemistry is an on-going challenge in the area. Of particular relevance are transformations that proceed in the absence of transition-metal reagents. In the current study, we report a comprehensive investigation of the coupling of nitrile imines and aryl boronic acids as an approach towards sustainable C?C bond formation. In situ generation of the highly reactive 1,3-dipole facilitates a Petasis–Mannich-type coupling via a nucleophilic boronate complex. The introduction of hydrazonyl chlorides as a complementary nitrile imine source to the 2,5-tetrazoles previously reported by our laboratory further broadens the scope of the approach. Additionally, we exemplify for the first time the extension of this protocol into another 1,3-dipole, through the synthesis of aryl ketone oximes from aryl boronic acids and nitrile N-oxides.
Divergent Synthesis of 1H-Indazoles and 1H-Pyrazoles from Hydrazones via Iodine-Mediated Intramolecular Aryl and sp3 C–H Amination
Wei, Wei,Wang, Zhen,Yang, Xikang,Yu, Wenquan,Chang, Junbiao
, p. 3378 - 3387 (2017/10/09)
A divergent intramolecular C–H amination of hydrazones has been developed employing molecular iodine (I2) as the sole oxidant. The required hydrazone substrates were readily obtained by condensation of hydrazines with the corresponding ketones.
[Bis-(trifluoroacetoxy)iodo]benzene-Mediated Oxidative Direct Amination C–N Bond Formation: Synthesis of 1H-Indazoles
Zhang, Zhiguo,Huang, Yuanyuan,Huang, Guoqing,Zhang, Guisheng,Liu, Qingfeng
, p. 2426 - 2433 (2017/07/24)
An efficient [bis-(trifluoroacetoxy)iodo]benzene (PIFA)-mediated oxidative C-N bond formation is developed for the synthesis of 1H-indazoles from readily available arylhydrazones. The reaction tolerates a wide range of functional groups and has broad scope of substrates. Moreover, this method is a relative green and reliable method for rapid preparation of substituted 1H-indazoles under mild conditions.
An efficient transition-metal-free synthesis of 1H-indazoles from arylhydrazones with montmorillonite K-10 under O2 atmosphere
Yu, Jin,Lim, Jin Woo,Kim, Su Yeon,Kim, Jimin,Kim, Jae Nyoung
supporting information, p. 1432 - 1436 (2015/03/04)
An efficient transition-metal-free synthetic method of 1H-indazoles has been developed. The reaction of arylhydrazones in the presence of montmorillonite K-10 in 1,2-dichlorobenzene at 130 °C afforded 1H-indazoles in good yields most likely via a sequenti
Facile access to 1H-indazoles through iodobenzene-catalyzed C-H amination under mild, transition-metal-free conditions
Kashiwa, Mitsuhiro,Sonoda, Motohiro,Tanimori, Shinji
supporting information, p. 4720 - 4723 (2014/08/05)
The transition-metal- and halogen-free synthesis of N-aryl-substituted 1H-indazole and derivatives was accomplished on the basis of the iodobenzene-catalyzed intramolecular C-H amination of hydrazones under mild conditions. Reactions of hydrazones derived
Synthesis of 1 H-indazoles and 1 H-pyrazoles via FeBr3/O 2 mediated intramolecular C-H amination
Zhang, Tianshui,Bao, Weiliang
, p. 1317 - 1322 (2013/04/10)
A new synthesis of substituted 1H-indazoles and 1H-pyrazoles from arylhydrazones via FeBr3/O2 mediated C-H activation/C-N bond formation reactions is reported. The corresponding 1,3-diaryl-substituted indazoles and trisubstituted pyr
