Rhodium-Catalyzed Enantio- and Regioselective Allylation of In-doles with gem-Difluorinated Cyclopropanes

09 February 2024, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


The use of gem-difluorinated cyclopropanes (gem-DFCPs) as fluoroallyl surrogates under transition-metal catalysis has drawn considerable attention recently but such reac-tions are restricted to producing achiral or racemic mono-fluoroalkenes. Herein, we report the first enantioselective allylation of indoles with gem-DFCPs under rhodium catal-ysis. This reaction shows exceptional branched regioselec-tivity towards rhodium catalysis with gem-DFCPs, which provides an efficient route to enantioenriched fluoroal-lylated indoles with wide substrate scope and good func-tional group tolerance.


gem-difluorinated cyclopropanes
rhodium catalysis
allylation reaction
branched regioselectivity

Supplementary materials

Supporting Information
Detailed experimental procedures, characterization data, copies of 1H, 13C, 19F NMR and HPLC spectra of products are reported in the Supporting Information.


Comments are not moderated before they are posted, but they can be removed by the site moderators if they are found to be in contravention of our Commenting Policy [opens in a new tab] - please read this policy before you post. Comments should be used for scholarly discussion of the content in question. You can find more information about how to use the commenting feature here [opens in a new tab] .
This site is protected by reCAPTCHA and the Google Privacy Policy [opens in a new tab] and Terms of Service [opens in a new tab] apply.