1419611-75-8Relevant articles and documents
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.
[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.
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