65864-99-5Relevant academic research and scientific papers
Continuous Flow Synthesis and Purification of Aryldiazomethanes through Hydrazone Fragmentation
Lévesque, éric,Laporte, Simon T.,Charette, André B.
, p. 837 - 841 (2017/01/14)
Electron-rich diazo compounds, such as aryldiazomethanes, are powerful reagents for the synthesis of complex structures, but the risks associated with their toxicity and instability often limit their use. Flow chemistry techniques make these issues avoidable, as the hazardous intermediate can be used as it is produced, avoiding accumulation and handling. Unfortunately, the produced stream is often contaminated with other reagents and by-products, making it incompatible with many applications, especially in catalysis. Herein is reported a metal-free continuous flow method for the production of aryldiazomethane solutions in a non-coordinating solvent from easily prepared, bench-stable sulfonylhydrazones. All by-products are removed by an in-line aqueous wash, leaving a clean, base-free diazo stream. Three successful sensitive metal-catalyzed transformations demonstrated the value of the method.
Rapid Asymmetric Synthesis of Disubstituted Allenes by Coupling of Flow-Generated Diazo Compounds and Propargylated Amines
Poh, Jian-Siang,Makai, Szabolcs,von Keutz, Timo,Tran, Duc N.,Battilocchio, Claudio,Pasau, Patrick,Ley, Steven V.
, p. 1864 - 1868 (2017/02/05)
We report herein the asymmetric coupling of flow-generated unstabilized diazo compounds and propargylated amine derivatives, using a new pyridinebis(imidazoline) ligand, a copper catalyst and base. The reaction proceeds rapidly, generating chiral allenes in 10–20 minutes with high enantioselectivity (89–98 % de/ee), moderate yields and a wide functional group tolerance.
Iterative reactions of transient boronic acids enable sequential C-C bond formation
Battilocchio, Claudio,Feist, Florian,Hafner, Andreas,Simon, Meike,Tran, Duc N.,Allwood, Daniel M.,Blakemore, David C.,Ley, Steven V.
, p. 360 - 367 (2016/04/04)
The ability to form multiple carbon-carbon bonds in a controlled sequence and thus rapidly build molecular complexity in an iterative fashion is an important goal in modern chemical synthesis. In recent times, transition-metal-catalysed coupling reactions
A Versatile Room-Temperature Route to Di- and Trisubstituted Allenes Using Flow-Generated Diazo Compounds
Poh, Jian-Siang,Tran, Duc N.,Battilocchio, Claudio,Hawkins, Joel M.,Ley, Steven V.
, p. 7920 - 7923 (2015/06/30)
A copper-catalyzed coupling reaction between flow-generated unstabilized diazo compounds and terminal alkynes provides di- and trisubstituted allenes. This extremely mild and rapid transformation is highly tolerant of several functional groups. Well tolerated: A mild copper-catalyzed coupling reaction between unstabilized diazo compounds (generated in flow) and terminal alkynes is reported. The method provides di- and trisubstituted allenes with high functional-group tolerance.
Cyclopropanation using flow-generated diazo compounds
Roda, Nuria M.,Tran, Duc N.,Battilocchio, Claudio,Labes, Ricardo,Ingham, Richard J.,Hawkins, Joel M.,Ley, Steven V.
, p. 2550 - 2554 (2015/11/17)
We have devised a room temperature process for the cyclopropanation of electron-poor olefins using unstabilised diazo compounds, generated under continuous flow conditions. This protocol was applied to a wide range of different diazo species to generate f
An enantioselective synthesis of 2-aryl cycloalkanones by sc-catalyzed carbon insertion
Rendina, Victor L.,Moebius, David C.,Kingsbury, Jason S.
, p. 2004 - 2007 (2011/07/07)
Current methods for asymmetric α-arylation require blocking groups to prevent reaction at the R0-carbon, basic conditions that promote racemization, or multistep synthesis. This work records the first catalytic enantioselective examples of the diazoalkane-carbonyl homologation reaction. Medium ring 2-aryl ketones are prepared in one step in up to 98:2 er and 99% yield from the unsubstituted lower homologue by Sc-catalyzed aryldiazomethyl insertion with simple bis- and tris(oxazoline) ligands.
Synthesis of some fenchyl-substituted alkenes and enol-ethers containing 3-oxyphenyl substituents by the barton-kellogg reaction
Ciscato, Luiz Francisco M. L.,Bastos, Erick L.,Bartoloni, Fernando H.,Gu?nther, Wolfgang,Weiss, Dieter,Beckert, Rainer,Baader, Wilhelm Josef
experimental part, p. 1896 - 1904 (2011/02/22)
The synthesis of one fenchyl-substituted alkene and two enol-ethers, containing 3-oxyphenyl substituents by the Barton-Kellogg reaction is described. The tri-substituted aromatic fenchyl-alkene 1a was prepared in 53percent yield from thiofenchone and a di
