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Regiocontrolled Halogen Dance and In Situ Transmetalation of Pyrroles Directed by the α-Substituent.
- Source :
- Synlett; Oct2024, Vol. 35 Issue 16, p1919-1923, 5p
- Publication Year :
- 2024
-
Abstract
- Multiply substituted pyrroles are found in medicines, natural products, and functional materials. A general method for introducing functionality on the pyrrole ring is thus required. Herein, a regiocontrolled halogen dance reaction and an in situ transmetalation of α-functionalized bromopyrroles are reported. Selective generation of the isomeric pyrrolylmetal species was achieved by using an ethyl ester or a phenyl group at the α-position of the pyrrole and by switching between the halogen dance reaction and in situ transmetalation. These reactions proceeded smoothly when an N , N -dimethylsulfamoyl group was attached to the pyrrole nitrogen atom, providing the corresponding products in 68% to quantitative yields on 1-mmol scale. This method was applicable to the formal synthesis of Kendine 91. [ABSTRACT FROM AUTHOR]
- Subjects :
- PYRROLES
HALOGENS
PHENYL group
NATURAL products
ETHYL esters
Subjects
Details
- Language :
- English
- ISSN :
- 09365214
- Volume :
- 35
- Issue :
- 16
- Database :
- Complementary Index
- Journal :
- Synlett
- Publication Type :
- Academic Journal
- Accession number :
- 179597902
- Full Text :
- https://doi.org/10.1055/a-2236-1060