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Et2Zn-Mediated Radical (3 + 2) Cycloaddition of Vinyl Azides with Ethyl Iododifluoroacetate to Access 3,3-Difluoro-γ-lactams.

Journal of Organic Chemistry, 2023
A diethylzinc-mediated radical (3 + 2) cycloaddition of vinyl azides with ethyl iododifluoroacetate is presented. The developed reaction features good functional group tolerance, broad substrate scope, and operational simplicity, enabling efficient ...
Yifei Zhang   +3 more
semanticscholar   +1 more source

Triplet Sensitized Photolysis of a Vinyl Azide: Direct Detection of a Triplet Vinyl Azide and Nitrene

The Journal of Organic Chemistry, 2014
Photolysis of vinylazide 1, which has a built-in acetophenone triplet sensitizer, in argon-saturated toluene results in azirine 2, whereas irradiation in oxygen-saturated toluene yields cyanide derivatives 3 and 4. Laser flash photolysis of azide 1 in argon-saturated acetonitrile shows formation of vinylnitrene 1c, which has a λmax at ∼300 nm and a ...
Sridhar, Rajam   +11 more
openaire   +5 more sources

Synthesis of Azabicyclo[3.1.1]heptenes Enabled by Catalyst-Controlled Annulations of Bicyclo[1.1.0]butanes with Vinyl Azides.

Journal of the American Chemical Society
Bridged bicyclic scaffolds are emerging bioisosteres of planar aromatic rings under the concept of "escape from flatland". However, adopting this concept into the exploration of bioisosteres of pyridines remains elusive due to the challenge of ...
Zhongren Lin   +4 more
semanticscholar   +1 more source

Iridium-Catalyzed Enantioselective and Chemodivergent Allenylic Alkylation of Vinyl Azides for the Synthesis of α-Allenylic Amides and Ketones.

Angewandte Chemie, 2022
The first enantioselective synthesis of α-allenylic amides and ketones through allenylic alkylation of vinyl azides is reported. In these chemodivergent reactions, cooperatively catalyzed by a Ir(I)/(phosphoramidite,olefin) complex and Sc(OTf)3, vinyl ...
Aditya Chakrabarty, S. Mukherjee
semanticscholar   +1 more source

A Route to the Mild Synthesis of α-Selenomethylketones via Vinyl Azides.

Journal of Organic Chemistry
Organic selenium compounds are important molecules with a wide range of applications in pharmaceuticals, organic materials, catalysis, and other fields.
Shuting Zhang   +6 more
semanticscholar   +1 more source

Access to [2.2]Paracyclophane-Fused N-Heterocycles via Palladium-Catalyzed C-H Activation and Cyclization of [2.2]Paracyclophaneacylhydrazones with Vinyl Azides.

Organic Letters
A novel protocol for the synthesis of [2.2]paracyclophane-fused N-heterocycles via palladium-catalyzed C-H activation and cyclization of [2.2]paracyclophaneacylhydrazones with vinyl azides has been developed. High regioselectivity control was realized by
Biao Nie   +3 more
semanticscholar   +1 more source

Decatungstate-Catalyzed Photochemical Synthesis of Enaminones from Vinyl Azides and Aldehydes.

Organic Letters, 2022
Visible light-induced synthesis of enaminones from vinyl azides and aldehydes under decatungstate photocatalysis was developed. The reaction proceeds via acyl radical generation from aldehyde, followed by its addition to vinyl azide, nitrogen elimination,
S. Paveliev   +4 more
semanticscholar   +1 more source

Computational Study on the Vinyl Azide Decomposition

The Journal of Physical Chemistry A, 2014
The decomposition mechanism of vinyl azide (CH2CHN3) has been studied by calculations of the electronic structure. In addition, a study based on the topology of the electron charge density distribution and its Laplacian function, within the Quantum Theory of Atoms in Molecules (QTAIM), has been carried out with the aim of comprehending the electron ...
Darío J R, Duarte   +2 more
openaire   +2 more sources

Electrochemical Synthesis of Ketones via Metal-Free Decarboxylative Coupling of Vinyl Azides and NHPI Esters

Synlett : Accounts and Rapid Communications in Synthetic Organic Chemistry
We introduce a metal-free method for C–C bond formation by coupling NHPI esters with vinyl azides through electrochemical synthesis. By converting carboxylic acids into radical-initiating NHPI esters, our approach achieves efficient C(sp³)–C(sp 3 ) bond ...
Bhawana Jat   +3 more
semanticscholar   +1 more source

Redox-Neutral Generation of Iminyl Radicals by N-Heterocyclic Carbene Catalysis: Rapid Access to Phenanthridines from Vinyl Azides.

Organic Letters, 2022
An N-heterocyclic carbene-catalyzed oxidant-, metal- and light-free iminyl radical generation pathway stemming from the reaction of vinyl azide and α-bromo ester is uncovered.
Lixia Liu, Qijing Zhang, Chengming Wang
semanticscholar   +1 more source

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