Abstract
The Adler-Becker reaction is a useful approach for the oxidative dearomatization of salicylic alcohols to spiroepoxydienones and has been applied in the total synthesis of several natural products. Despite the advantages, the substrate and product instability under the reaction conditions can decrease the reaction efficiency, leading to lower yields. Herein, we report the Adler-Becker reaction in a continuous flow for the transformation of reduced salicylaldehydes into spiroepoxydienones in a one-pot approach. For that, a heterogeneous oxidant based on periodate is developed, leading to an efficient continuous flow process, with higher productivity and shorter reaction times, when compared with batch conditions.
| Original language | English |
|---|---|
| Pages (from-to) | 11570-11577 |
| Number of pages | 8 |
| Journal | ACS Omega |
| Volume | 7 |
| Issue number | 14 |
| DOIs | |
| Publication status | Published - 12 Apr 2022 |
Bibliographical note
Publisher Copyright:© 2022 The Authors. Published by American Chemical Society and Division of Chemical Education, Inc.
Funding
The authors thank Funda??o para a Ci?ncia e Tecnologia (FCT) (ref PTDC/QUI-QOR/32008/2017, PTDC/CTM-CTM/29869/2017 UIDB/04138/2020, UIDP/04138/2020, UIDB/04567/2020, and UIDP/04567/2020) for financial support. The NMR spectrometers are part of the National NMR Network (PTNMR) and are partially supported by Infrastructure Project No 022161 (co-financed by FEDER through COMPETE 2020, POCI and PORL and FCT through PIDDAC). This project has received funding from the European Union's Horizon 2020 research and innovation programme under grant agreement No. 951996. The authors thank Fundac\u0327a\u0303o para a Cie\u0302ncia e Tecnologia (FCT) (ref PTDC/QUI-QOR/32008/2017, PTDC/CTM-CTM/29869/2017, UIDB/04138/2020, UIDP/04138/2020, UIDB/04567/2020, and UIDP/04567/2020) for financial support. The NMR spectrometers are part of the National NMR Network (PTNMR) and are partially supported by Infrastructure Project No 022161 (co-financed by FEDER through COMPETE 2020, POCI and PORL and FCT through PIDDAC). This project has received funding from the European Union\u2019s Horizon 2020 research and innovation programme under grant agreement No. 951996.
| Funders | Funder number |
|---|---|
| Ci?ncia e Tecnologia | |
| Programa Operacional Temático Factores de Competitividade | |
| European Regional Development Fund | |
| Horizon 2020 | |
| Fundação para a Ciência e a Tecnologia | UIDP/04567/2020, PTDC/CTM-CTM/29869/2017 UIDB/04138/2020, UIDB/04567/2020, PTDC/QUI-QOR/32008/2017, 022161, PTDC/CTM-CTM/29869/2017, UIDP/04138/2020 |
| Fundação para a Ciência e Tecnologia | UIDB/04138/2020 |
| Horizon 2020 Framework Programme | 951996 |