1863-21-4Relevant articles and documents
Synthesis of 7-pentafluorophenyl-1 H -indole: An anion receptor for anion-π interactions
Sun, Zhan-Hu,Albrecht, Markus,Giese, Michael,Pan, Fangfang,Rissanen, Kari
, p. 2075 - 2077 (2014)
7-Pentafluorophenyl-1H-indole has the potential to be a key compound for the investigation of anion-π interactions in solution. Unfortunately, it was not possible to obtain it by aryl-aryl coupling reaction. Finally, it has been prepared by Bartoli indole synthesis. The key compound as well as analogues were submitted to preliminary studies of anion binding. Single crystals of two key receptors were obtained. Georg Thieme Verlag Stuttgart New York.
Intermolecular Nucleophilic Addition Reaction of a C-7 Anion from N -[Bis(dimethylamino)phosphoryl]indole to Electrophiles/Arynes: Synthesis of 7-Substituted Indoles
Kaur, Amarjit,Kaur, Babaldeep,Kaur, Manjot,Sharma, Esha,Singh, Kamal Nain,Singh, Paramjit
, p. 84 - 87 (2022/01/04)
A novel approach to the C-7 substitution of N-[bis(dimethylamino)phosphoryl]indole by nucleophilic addition of the corresponding C-7 carbanion to electrophiles or arynes is described. The directing group can be easily removed, providing a simple route to the synthesis of 7-functionalized indoles.
Catalytic C(sp2)?H amination reactions using dinickel imides
Andjaba, John M.,Powers, Ian G.,Uyeda, Christopher,Zeller, Matthias
supporting information, p. 3794 - 3801 (2020/11/23)
C?H amination reactions are valuable transformations for the construction of C?N bonds. Due to their relatively high bond dissociation energies, C(sp2)?H bonds are generally not susceptible toward direct nitrene insertion, necessitating alternative mechanisms for C?H activation. Here, we report that cationic dinuclear (NDI)Ni2 (NDI = naphthyridine?diimine) complexes catalyze intramolecular nitrene insertions into aryl and vinyl C(sp2)? H bonds. Mechanistic studies suggest that a bridging imido ligand supported at a Ni2 site induces C?H activation by a 1,2-addition pathway to generate an azametallacyclic intermediate. This organometallic mechanism contrasts with the electrocyclization/1,2-shift mechanism proposed for analogous transformations using Rh2 catalysts. The implications of these mechanistic differences for the stereoselectivity and chemoselectivity of C?H amination are described.