373596-95-3Relevant academic research and scientific papers
Rhodium(III)-catalyzed [4+2] annulation via C-H activation: Synthesis of multi-substituted naphthalenone sulfoxonium ylides
Song, Xiaohan,Han, Xu,Zhang, Rui,Liu, Hong,Wang, Jiang
, (2019)
A convenient Rh(III)-catalyzed C-H activation and cascade [4+2] annulation for the synthesis of naphthalenone sulfoxonium ylides has been developed. This method features perfect regioselectivity, mild and redox-neutral reaction conditions, and broad substrate tolerance with good to excellent yields. Preliminary mechanistic experiments were conducted and a plausible reaction mechanism was proposed. The new type naphthalenone sulfoxonium ylides could be further transformed into multi-substituted naphthols, which demonstrates the practical utility of this methodology.
Rhodium(i)-catalyzed vinylation/[2 + 1] carbocyclization of 1,6-enynes with α-diazocarbonyl compounds
Huang, Junmin,Hu, Xinwei,Chen, Fengjuan,Gui, Jiao,Zeng, Wei
supporting information, p. 7042 - 7054 (2019/08/01)
A sequential Rh(i)-catalyzed vinylation/[2 + 1]carbocyclization between enynes and diazo compounds has been developed. This transformation features a wide range of enynes and acceptor/acceptor diazo compounds, providing easy access to versatile vinyl-substituted azabicyclo[3.1.0]hexanes having a broad tolerance to functional groups.
Electronic effects in migratory groups. [1,4]- versus [1,2]-rearrangement in rhodium carbenoid generated bicyclic oxonium ylides
Karche,Jachak,Dhavale
, p. 6323 - 6332 (2007/10/03)
The variety of α-diazo β-keto esters (3a-f, 8a-f) with varying substituents (ED/EW) on the phenyl ring of the O-benzyl group were prepared. The rhodium(II) acetate catalyzed decomposition of diazo compounds in benzene reflux conditions. The ratio of 1,4 versus 1,2 migration product was determined. It was found that an increase in electron density on the benzylic carbon of the migrating group prefers 1,4 migration products (4, 9) while a decrease in electron density leads to a preponderance of 1,2 migration products (5, 10). The results obtained were correlated to the mechanistic aspect of the product selectivity. The intermediacy of the intramolecular oxonium ylide formation was demonstrated by crossover experiments. The preference for the formation of 2,3 sigmatropic rearrangement product over 1,2 and 1,4 was demonstrated by performing the reaction with α-diazo β-keto esters (13a, 13b) with O-allyl and O-propargyl at C3. The effect of solvent, temperature, and mole percentage of rhodium(II) acetate was also studied.
