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Regiocontrolled Halogen Dance and In Situ Transmetalation of Pyrroles Directed by the α-Substituent.

Authors :
Matsuyama, Daichi
Okumi, Tatsuki
Mori, Atsunori
Okano, Kentaro
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]

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