1073483-49-4Relevant academic research and scientific papers
Iridium-Catalyzed Enantioselective α-Allylic Alkylation of Amides Using Vinyl Azide as Amide Enolate Surrogate
Chakrabarty, Aditya,Mukherjee, Santanu
, p. 7752 - 7756 (2020)
Among the unstabilized enolates used as nucleophiles in iridium-catalyzed asymmetric allylic alkylation reactions, amide enolates are the least explored. Vinyl azides are now employed as amide enolate surrogates in Ir-catalyzed asymmetric allylic alkylation with branched allylic alcohols as the allylic electrophile. Competing reaction pathways are suppressed through the systematic tuning of the steric and electronic properties of vinyl azide to effect the α-allylic alkylation of secondary acetamides with high atom economy, exclusive branched selectivity, and mostly excellent enantioselectivity.
Cerium(IV) ammonium nitrate promoted synthesis of O-phthalimide oximes from vinyl azides and N-hydroxyphthalimide
Paveliev, Stanislav A.,Alimkhanova, Liliya S.,Sergeeva, Anna V.,Terent'ev, Alexander O.
, (2020)
O-Phthalimide oximes with an N–O–N fragment were synthesized in high yields via the reaction of vinyl azides with phthalimide-N-oxyl radicals derived from N-hydroxyphthalimide under the action of cerium(IV) ammonium nitrate. The disclosed process is based on the radical transformation of vinyl azides with the elimination of nitrogen and the formation of iminyl N-radicals. The developed approach exploited the dual reactivity of imide-N-oxyl radicals. They act as O-components for oxidative C–O coupling with vinyl azides and participate in subsequent formation of the N–O bond via their recombination with intermediate iminyl radicals.
Electrochemical Synthesis of O-Phthalimide Oximes from α-Azido Styrenes via Radical Sequence: Generation, Addition and Recombination of Imide-N-Oxyl and Iminyl Radicals with C?O/N?O Bonds Formation
Paveliev, Stanislav A.,Churakov, Artem I.,Alimkhanova, Liliya S.,Segida, Oleg O.,Nikishin, Gennady I.,Terent'ev, Alexander O.
supporting information, p. 3864 - 3871 (2020/07/30)
Electrochemically induced radical-initiated reaction of vinyl azides with N-hydroxyphthalimide resulting O-phthalimide oximes with challenging for organic chemistry N?O-N fragment has been discovered. The developed approach introduces in synthesis electrochemically generated O-centered imide-N-oxyl radicals as the coupling components. Sequential formation of C?O and N?O bonds was achieved via generation and selective addition of imide-N-oxyl radicals, followed by recombination with iminyl radicals. A wide range of O-phthalimide oximes was obtained with the yields up to 84percent. (Figure presented.).
[1+1+3] Annulation of Diazoenals and Vinyl Azides: Direct Synthesis of Functionalized 1-Pyrrolines through Olefination
Kanchupalli, Vinaykumar,Katukojvala, Sreenivas
, p. 5433 - 5437 (2018/04/09)
A dirhodium carboxylate catalyzed [1+1+3] annulation reaction of diazoenals and vinyl azides that gives synthetically important enal-functionalized 1-pyrroline derivatives was developed. The reaction involves a novel rhodium-catalyzed olefination of diazoenals with vinyl azides via electrophilic enal carbenoids, resulting in a new class of enal acrylates. The annulation reaction was used for the direct synthesis of valuable deuterated 1-pyrrolines. Structural diversification of the enal-functionalized 1-pyrrolines resulted in the biologically important pyrrolidine-fused oxaziridine, amino acid derivatives, and a 6-azabicyclo[3.2.1]octane motif present in polycyclic alkaloids.
Tf 2 NH-Catalyzed 1,6-Conjugate Addition of Vinyl Azides with p -Quinone Methides: A Mild and Efficient Method for the Synthesis of β-Bis-Arylamides
Rathod, Jayant,Sharma, Brijesh M.,Mali, Pramod S.,Kumar, Pradeep
supporting information, p. 5224 - 5230 (2017/10/06)
Tf 2 NH-catalyzed tandem 1,6-conjugate addition/Schmidt type rearrangement using vinyl azides and p -quinone methides to access a variety of β-bis-arylated amides is reported. The method is quick, efficient, mild, and high yielding with broad substrate scope.
Photoredox-catalysed redox-neutral trifluoromethylation of vinyl azides for the synthesis of α-trifluoromethylated ketones
Qin, Hai-Tao,Wu, Shu-Wei,Liu, Jia-Li,Liu, Feng
, p. 1696 - 1699 (2017/02/10)
A redox-neutral, mild, and simple protocol is developed for the synthesis of α-trifluoromethylated ketones from vinyl azides under transition-metal-free conditions. In the presence of organic photoredox catalyst N-methyl-9-mesityl acridinium and sodium trifluoromethanesulfinate, a broad range of substituted vinyl azides were found to react smoothly upon visible-light irradiation, readily furnishing the corresponding products in satisfied yields.
Synthesis of α-Fluoroketones from Vinyl Azides and Mechanism Interrogation
Wu, Shu-Wei,Liu, Feng
, p. 3642 - 3645 (2016/08/16)
An efficient and mild fluorination of vinyl azides for the synthesis of α-fluoroketones is described. The mechanistic studies indicated that a single-electron transfer (SET) and a subsequent fluorine atom transfer process could be involved in the reaction.
Copper-catalyzed c-h functionalization of pyridines and isoquinolines with vinyl azides: Synthesis of imidazo heterocycles
Donthiri, Ramachandra Reddy,Pappula, Venkatanarayana,Reddy, N. Naresh Kumar,Bairagi, Dipayan,Adimurthy, Subbarayappa
, p. 11277 - 11284 (2015/01/08)
Copper(I) iodide-catalyzed oxidative C(sp2)-H functionalization of pyridines and isoquinolines for the synthesis of imidazo[1,2-a]pyridines and 2-phenylimidazo[2,1-a]isoquinolines with vinyl azides under mild aerobic conditions is reported. Goo
