| Full text | |
| Author(s): |
Chiavegatti Neto, Attilio
;
Soares, Kelly Cintra
;
Santos, Maiara da Silva
;
Aimola, Tulio Jardini
;
Ferreira, Antonio Gilberto
;
Jardim, Guilherme A. M.
;
Tormena, Claudio Francisco
;
Paixao, Marcio Weber
;
Barbosa Ferreira, Marco Antonio
Total Authors: 9
|
| Document type: | Journal article |
| Source: | ORGANIC & BIOMOLECULAR CHEMISTRY; v. N/A, p. 8-pg., 2022-03-30. |
| Abstract | |
Herein, we report a fully detailed mechanistic study involving an organocatalyzed 1,3-dipolar cycloaddition via enolate or stabilized vinylogous carbanion intermediates and azide for the synthesis of 1,2,3-triazoles. A detailed investigation of the elementary steps, intermediates, and transition states of the two organocatalyzed metal-free click reactions is supported by DFT calculations and H-1 NMR monitoring experiments, providing detailed profiles for both reaction mechanisms. Distortion-interaction activation-strain (DIAS) analysis was also employed to further elucidate the regioselectivity in both reactions. (AU) | |
| FAPESP's process: | 14/15839-9 - Mechanistic studies of the 1,3-dipolar cycloaddition (3 +2) reaction between azides and alkylidene-malononitriles: A theoretical investigation. |
| Grantee: | Túlio Jardini Aímola |
| Support Opportunities: | Scholarships in Brazil - Scientific Initiation |
| FAPESP's process: | 18/01211-9 - Theoretical study of the mechanism of cycloaddition (3 + 2) reactions involving enolates and azides |
| Grantee: | Attilio Chiavegatti Neto |
| Support Opportunities: | Scholarships in Brazil - Scientific Initiation |
| FAPESP's process: | 20/10246-0 - Nuclear magnetic resonance spectroscopy: from pulse sequences to structural assignments |
| Grantee: | Claudio Francisco Tormena |
| Support Opportunities: | Research Projects - Thematic Grants |
| FAPESP's process: | 14/50249-8 - Green chemistry: sustainable synthetic methods employing benign solvents, safer reagents, and bio-renewable feedstock |
| Grantee: | Arlene Gonçalves Corrêa |
| Support Opportunities: | Research Grants - Applied Research Centers Program |
| FAPESP's process: | 20/01255-6 - Application of statistical tools in catalysis for understanding and predicting organic reactions |
| Grantee: | Marco Antonio Barbosa Ferreira |
| Support Opportunities: | Regular Research Grants |
| FAPESP's process: | 16/24726-9 - Estudos cinéticos em reacõeses de cicloadição (3+2) na preparação de 1,2,3-triazóis substituídos |
| Grantee: | Kelly Cintra Soares |
| Support Opportunities: | Scholarships in Brazil - Scientific Initiation |
| FAPESP's process: | 20/13563-7 - Prediction and design of catalytic processes using statistical modeling |
| Grantee: | Attilio Chiavegatti Neto |
| Support Opportunities: | Scholarships in Brazil - Doctorate (Direct) |