Journal article
Single point activation of pyridines enables reductive hydroxymethylation
- Abstract:
- The single point activation of pyridines, using an electron-deficient benzyl group, facilitates the ruthenium-catalysed dearomative functionalisation of a range of electronically diverse pyridine derivatives. This transformation delivers hydroxymethylated piperidines in good yields, allowing rapid access to medicinally relevant small heterocycles. A noteworthy feature of this work is that paraformaldehyde acts as both a hydride donor and an electrophile in the reaction, enabling the use of cheap and readily available feedstock chemicals. Removal of the activating group can be achieved readily, furnishing the free NH compound in only 2 steps. The synthetic utility of the method was illustrated with a synthesis of (±)-Paroxetine.
- Publication status:
- Published
- Peer review status:
- Peer reviewed
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(Preview, Version of record, pdf, 985.9KB, Terms of use)
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(Preview, Supplementary materials, pdf, 11.0MB, Terms of use)
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- Publisher copy:
- 10.1039/d0sc05656a
Authors
- Publisher:
- Royal Society of Chemistry
- Journal:
- Chemical Science More from this journal
- Volume:
- 12
- Pages:
- 742-746
- Publication date:
- 2020-11-16
- Acceptance date:
- 2020-11-10
- DOI:
- EISSN:
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2041-6539
- ISSN:
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2041-6520
- Language:
-
English
- Keywords:
- Pubs id:
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1146175
- Local pid:
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pubs:1146175
- Deposit date:
-
2020-11-20
- ARK identifier:
Terms of use
- Copyright holder:
- The Royal Society of Chemistry
- Copyright date:
- 2020
- Rights statement:
- © The Royal Society of Chemistry 2020. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
- Licence:
- CC Attribution (CC BY)
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