83922-78-5Relevant academic research and scientific papers
Overcoming Scope Limitations in Cross-Coupling of Diazo Nucleophiles by Manipulating Catalyst Speciation and Using Flow Diazo Generation
Sullivan, Ryan J.,Freure, Garrett P.R.,Newman, Stephen G.
, p. 5623 - 5630 (2019/06/05)
The accessible scope of palladium-catalyzed diazo cross-coupling reactions has been expanded to include aryl chlorides by controlled diazo slow addition. The success of this strategy is based on manipulating speciation within the catalytic cycle through starvation of the diazo reagent to make the Pd(II) oxidative intermediate the resting state. The strategy is also applicable to cross-coupling reactions with aryl bromides and, in combination with safe, on-demand flow generation of nonstabilized diazo reagents, has been used to greatly expand the scope of applicable diazo compounds for this chemistry as well. Lastly, DFT calculations have provided insight into the mechanism and support for the proposed explanation for success of the slow addition strategy.
Conversions of hydrazones to diazo compounds by n-butyllithium and azidotris(diethylamino)phosphonium bromide
McGuiness, Mark,Shechter, Harold
, p. 8425 - 8427 (2007/10/03)
Lithium hydrazonides, prepared by reactions of hydrazones with n-BuLi/hexane in THF at -78°C, are converted by azidotris(diethylamino)phosphonium bromide in THF at ～0°C efficiently, rapidly, and safely to their corresponding diazo compounds along with tri
1,2-Hydrogen migration and alkene formation in the photoexcited states of alkylphenyldiazomethanes
?elebi, Sol,Leyva, Soccoro,Modarelli, David A.,Platz, Matthew S.
, p. 8613 - 8620 (2007/10/02)
Laser flash photolysis of alkylphenyldiazomethanes in the presence of pyridine produces easily detected ylides. The data indicate that photolysis of alkylphenyldiazomethanes leads to both carbene formation and direct formation of rearrangement products which do not derive from relaxed carbene intermediates.
CYCLOADDITIONS OF DISUBSTITUTED DIAZO COMPOUNDS TO P-CHLORO(BISTRIMETHYLSILYL) METHYLENE PHOSPHINE.
Thoraval, J. Y.,Nagai, W.,Yeung Lam Ko, Y. Y. C.,Carrie, R.
, p. 3859 - 3868 (2007/10/02)
Disubstituted diazo compounds rapidly add to P-chloro (bistrimethylsilyl) methylene phosphine at low temperature. 1H, 31P and 13C NMR allow the characterization of the resulting cycloadducts and the establisment of the stereochemistry of the resulting cycloadducts which are potential precursors of ?3λ5 bis methylene phosphorane by nitrogen extrusion.
