64431-75-0Relevant academic research and scientific papers
Stereoselective Desymmetrization of gem-Diborylalkanes by “Trifluorination”
Kumar, Nivesh,Reddy, Reddy Rajasekhar,Masarwa, Ahmad
supporting information, p. 8008 - 8012 (2019/05/28)
An efficient and general method for the chemoselective synthesis of unsymmetrical gem-diborylalkanes is reported. This method is based on a late-stage desymmetrization through nucleophilic “trifluorination”, providing chiral gem-diborylalkanes bearing a trifluoroborate group. The reaction offers a highly modular and diastereoselective approach towards the synthesis of gem-diborylcyclopropanes. The utility of the gem-diborylalkane building blocks was demonstrated by selective post-functionalization of the trifluoroborate group. These functionalizations include inter- and intra- Pd-catalyzed Suzuki–Miyaura coupling reactions.
Safe and Facile Access to Nonstabilized Diazoalkanes Using Continuous Flow Technology
Rullière, Pauline,Benoit, Guillaume,Allouche, Emmanuelle M. D.,Charette, André B.
, p. 5777 - 5782 (2018/05/14)
Despite the high synthetic potential of nonstabilized diazo compounds, their utilization has always been hampered by stability, toxicity, and safety issues. The present method opens up access to the most reactive nonstabilized diazoalkanes. Among diazo compounds, nonstabilized alkyl diazo compounds are the least represented because of their propensity to degrade during preparation. The continuous flow oxidation process of hydrazones on a silver oxide column afforded an output stream of base- and metal-free pure diazo solution in dichloromethane. Starting from innocuous ketones and aldehydes, this methodology allows the production of a broad range of unprecedented diazoalkanes compounds in excellent yields, while highlighting their synthetic potential and the possibility of safe large-scale diazo production.
Diazo preparation via dehydrogenation of hydrazones with "activated" DMSO
Javed, Muhammad I.,Brewer, Matthias
, p. 1789 - 1792 (2008/02/02)
We report that "activated" dimethyl sulfoxide efficiently dehydrogenates hydrazones to the respective diazo species at -78°C. Under optimized conditions, triethylamine hydrochloride is removed quantitatively by vacuum filtration to provide solutions of diazo compounds. Stable diazo species can be isolated in high yield, or alternatively, the direct treatment of these solutions with carboxylic acids provides esters.
Advantageous Syntheses of Diazo Compounds by Oxidation of Hydrazones with Lead Tetraacetate in Basic Environments
Holton, Terrence L.,Shechter, Harold
, p. 4725 - 4729 (2007/10/02)
Varied sensitive diazo compounds 3 are produced efficiently and safely in 3-6 g quantities by oxidation (eq 1) of hydrazones 1 at -78 deg C with lead tetraacetate (2) in triethylamine/chloroform, N-methylmorpholine/dimethylformamide, tetramethylguanidine (8)/dimethylformamide, and tetramethylguanidine/methylene chloride, respectively, upon use of appropriate workup and handling techniques.New and improved nonhazardous procedures have been developed for preparing and handling hydrazones 1 from aldehydes and ketones in reactions with excess hydrazine.
