Formal C5-Alkylation of Indoles with Donor–Acceptor Cyclopropanes
Abstract
Installing an indole C5 substituent bearing multiple reactive functional groups, either directly via S E Ar or any other methods or during indole construction using classic methods, remains challenging due to the inherently low reactivity at this position or limited functional-group tolerance. Reported herein is a mild, regioselective C5-alkylation of N -alkylindolines with donor–acceptor cyclopropanes (DACs), providing efficient access to C5-alkylated indolines. Selected products were then transformed into the corresponding indoles through a DDQ oxidation–hydrogenation sequence, constituting a formal C5-alkylation of indoles with DACs.
Fields of Study & Subjects
Cyclopropane Reaction Mechanisms
Catalytic C–H Functionalization Methods
Catalytic Alkyne Reactions
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Volume
- 91
- Issue
- 7
- Pages
- 2865–2877
- Publication date
- 10 February 2026
- Language
- EN