| Full text | |
| Author(s): |
Camara, Viktor S.
;
da Silva, Aislan L.
;
da Luz, Lilian C.
;
Rodembusch, Fabiano S.
;
Santiago, Pedro H. O.
;
Ellena, Javier
;
Burtoloso, Antonio C. B.
Total Authors: 7
|
| Document type: | Journal article |
| Source: | ORGANIC LETTERS; v. 26, n. 5, p. 6-pg., 2024-01-29. |
| Abstract | |
The untapped potential of alpha-carbonyl sulfoxonium ylides in epoxide ring-opening reactions has been a notable gap in current research, with such reactivity predominantly associated with the highly reactive dimethylsulfoxonium methylide. This study introduces an innovative approach wherein an epoxide indole, formed in situ from 2-hydroxyindoline-3-triethylammonium bromide, undergoes reaction with alpha-ester sulfoxonium ylides. The outcome is the efficient synthesis of a range of 2-hydroxyindolin-3-ylidenes, demonstrating favorable yields (41-81%) and Z/E ratios from 4:1 to those of exclusive Z isomers. Additionally, the photophysical properties of the synthesized indolinylidenes are explored, along with their derivatization using various nucleophiles under acid catalysis. (AU) | |
| FAPESP's process: | 20/15230-5 - Research Centre for Greenhouse Gas Innovation - RCG2I |
| Grantee: | Julio Romano Meneghini |
| Support Opportunities: | Research Grants - Research Centers in Engineering Program |
| FAPESP's process: | 17/15850-0 - X-ray diffraction as a tool in potential drug development |
| Grantee: | Eduardo Ernesto Castellano |
| Support Opportunities: | Research Projects - Thematic Grants |
| FAPESP's process: | 21/10066-5 - Crystallographic and structural study of new substances with potential biological activities |
| Grantee: | Pedro Henrique de Oliveira Santiago |
| Support Opportunities: | Scholarships in Brazil - Post-Doctoral |
| FAPESP's process: | 22/00496-5 - Exploring the formation of new C-C bonds through reaction of sulfur ylides with epoxides and electrophilic species from alkenes |
| Grantee: | Viktor Saraiva Câmara |
| Support Opportunities: | Scholarships in Brazil - Post-Doctoral |
| FAPESP's process: | 23/02675-7 - New methodologies to form C-C bonds from sulfoxonium ylides |
| Grantee: | Antonio Carlos Bender Burtoloso |
| Support Opportunities: | Regular Research Grants |