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Palladium-Catalyzed Synthesis of Tricyclic Indoles via a N-S Bond Cleavage Strategy.
- Source :
-
Organic letters [Org Lett] 2021 Oct 01; Vol. 23 (19), pp. 7518-7523. Date of Electronic Publication: 2021 Sep 10. - Publication Year :
- 2021
-
Abstract
- In palladium/norbornene (Pd/NBE) chemistry, the " ortho effect" has been proven to be a key factor in the process of β-carbon elimination to extrude NBE. Herein, we found that the o -iodoaniline protected by a p -methoxybenzenesulfonyl group can recover the " ortho effect" and then undergo N-S bond cleavage with vinyl palladium, thus achieving a highly selective C-N coupling reaction in the Catallani-Lautens reaction system. On the basis of this discovery, a one-step synthesis of highly functionalized tricyclic indole derivatives was realized.
Details
- Language :
- English
- ISSN :
- 1523-7052
- Volume :
- 23
- Issue :
- 19
- Database :
- MEDLINE
- Journal :
- Organic letters
- Publication Type :
- Academic Journal
- Accession number :
- 34505792
- Full Text :
- https://doi.org/10.1021/acs.orglett.1c02715