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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Photoredox-Catalyzed Synthesis of Alkylaryldiazenes: Formal Deformylative C-N Bond Formation with Alkyl Radicals

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Author(s):
Angnes, Ricardo A. [1, 2] ; Potnis, Chinmay [2] ; Liang, Shengzong [2] ; Correia, Carlos Roque D. [1] ; Hammond, Gerald B. [2]
Total Authors: 5
Affiliation:
[1] Univ Estadual Campinas, Chem Inst, BR-13083970 Campinas, SP - Brazil
[2] Univ Louisville, Dept Chem, Louisville, KY 40292 - USA
Total Affiliations: 2
Document type: Journal article
Source: Journal of Organic Chemistry; v. 85, n. 6, p. 4153-4164, MAR 20 2020.
Web of Science Citations: 0
Abstract

Diazenes are valuable compounds that have found broad applicability because of their optical and biological properties. We report the synthesis of alkylaryldiazenes via formal, photoredox-catalyzed, deformylative C-N bond formation. The procedure employs dihydropyridines for the generation of alkyl radicals, which are then trapped by diazonium salts and reduced to the corresponding diazenes. Control experiments were performed to confirm the involvement of radicals in the mechanism. The reaction can be carried out at room temperature and employs readily available reagents; the mild conditions allowed the use of highly functionalized substrates. There was no observed tautomerization of the diazenes to the corresponding arylhydrazones. (AU)

FAPESP's process: 17/01779-2 - Powerful Partners: Ionic Promoters and the Enantioselective Heck-Matsuda Reaction
Grantee:Ricardo Almir Angnes
Support Opportunities: Scholarships abroad - Research Internship - Doctorate
FAPESP's process: 13/25849-9 - Application of the enantioselective Heck-Matsuda reaction for substrate oriented regioselective desymmetrizations
Grantee:Ricardo Almir Angnes
Support Opportunities: Scholarships in Brazil - Doctorate
FAPESP's process: 14/25770-6 - New frontiers in cross-coupling reactions promoted by palladium: combining enantioselective catalysis, C-H activations, new materials and in flux reactions aiming at high efficiency and sustainability in synthetic processes
Grantee:Carlos Roque Duarte Correia
Support Opportunities: Research Projects - Thematic Grants