Back to Search
Start Over
Pd-Catalyzed Cascade Heck/C(sp 3 )-H Activation for Spirocyclopropyl Oxindoles.
- Source :
-
Organic letters [Org Lett] 2024 Jun 21; Vol. 26 (24), pp. 5069-5073. Date of Electronic Publication: 2024 Jun 07. - Publication Year :
- 2024
-
Abstract
- We have demonstrated a Pd(0)-catalyzed Heck/C(sp <superscript>3</superscript> )-H activation cascade for the synthesis of spirocyclopropyl oxindoles in high yields from easily accessible ortho -bromoacrylamides. The formation of spirocyclopropyl oxindole is guided by an unconventional four-membered palladacycle through C(sp <superscript>3</superscript> )-H activation. The reaction exhibits a wide range of substrate scope and operates efficiently with a mere 0.5 mol % of Pd-catalyst. In addition, the use of microwave conditions facilitates rapid completion of the reaction. Furthermore, this spirocyclopropanation strategy can be coupled with [3 + 2] cycloaddition to produce spiropyrrolidine oxindoles, offering a valuable approach for the preparation of alkaloids such as (±)-horsfiline and (±)-coerulescine.
Details
- Language :
- English
- ISSN :
- 1523-7052
- Volume :
- 26
- Issue :
- 24
- Database :
- MEDLINE
- Journal :
- Organic letters
- Publication Type :
- Academic Journal
- Accession number :
- 38847514
- Full Text :
- https://doi.org/10.1021/acs.orglett.4c01017