120568-94-7Relevant articles and documents
Functionalization of Bis-Diazaphospholene P–P Bonds with Diverse Electrophiles
Huchenski, Blake S. N.,Robertson, Katherine N.,Speed, Alexander W. H.
, p. 5140 - 5144 (2020)
Phosphorus-sp3 or -sp2 carbon bonds are readily formed by the reaction of bis-diazaphospholenes with several classes of electrophiles. These reactions result in cleavage of the phosphorus–phosphorus bond and formation of functionalized diazaphospholenes. The reactions proceed rapidly, without catalysis. Experimental evidence with aryl and alkyl halides suggests the intermediacy of radicals in some cases, however other evidence suggests either radical or polar mechanisms may be operative for certain substrates, with a dependence on reaction conditions. In three cases, the product aryl diazaphospholenes have been shown to transfer the aryl substituent to electrophiles. These results reveal that diazaphospholene dimers are potent participants in radical chemistry with organic substrates at room temperature without requiring chemical initiators.
Site-Specific Oxidation of (sp3)C-C(sp3)/H Bonds by NaNO2/HCl
Zhao, Jianyou,Shen, Tong,Sun, Zhihui,Wang, Nengyong,Yang, Le,Wu, Jintao,You, Huichao,Liu, Zhong-Quan
supporting information, p. 4057 - 4061 (2021/05/26)
A site-specific oxidation of (sp3)C-C(sp3) and (sp3)C-H bonds in aryl alkanes by the use of NaNO2/HCl was explored. The method is chemical-oxidant-free, transition-metal-free, uses water as the solvent, and proceeds under mild conditions, making it valuable and attractive to synthetic organic chemistry.
Synthesis of All-Carbon Quaternary Centers by Palladium-Catalyzed Olefin Dicarbofunctionalization
Koy, Maximilian,Bellotti, Peter,Katzenburg, Felix,Daniliuc, Constantin G.,Glorius, Frank
supporting information, p. 2375 - 2379 (2020/01/24)
The redox-neutral dicarbofunctionalization of tri- and tetrasubstituted olefins to form a variety of (hetero)cyclic compounds under photoinduced palladium catalysis is described. This cascade reaction process was used to couple styrenes or acryl amides with a broad range of highly decorated olefins tethered to aryl or alkyl bromides (>50 examples). This procedure enables one or two contiguous all-carbon quaternary centers to be formed in a single step. The products could be readily diversified and applied in the synthesis of a bioactive oxindole analogue.
