N–N Atropisomer Synthesis via Electrolyte- and Base-Free Electrochemical Cobalt-Catalysed C–H Annulation

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

Abstract

Merging electrochemistry with asymmetric C−H activation has proven as an advantageous alternative to prepare valuable enantiopure molecules. However, established methods require a stoichiometric use of supporting electrolytes to promote electron transfer in solution and often additionally serve as a base to assist C−H bond cleavage, which are hazardous and would produce additional waste. Herein, we described an exogenous electrolyte- and base-free electrocatalytic atroposelective C–H annulation, providing facile and sustainable access to N–N axially chiral isoquinolinones in excellent enantioselectivities and good yields. This protocol is enabled by a combination of simple Co(OAc)2·4H2O and readily available chiral salicyloxazoline (Salox), proceeds well with 13 classes of alkynes, and tolerates a wealth of functional groups for streamlined transformations.

Keywords

electrochemistry
C–H activation
N–N atropisomer
cobalt catalysis
electrolyte- and base-free

Supplementary materials

Title
Description
Actions
Title
N–N Atropisomer Synthesis via Electrolyte- and Base-Free Electrochemical Cobalt-Catalysed C–H Annulation
Description
Supplementary Information for N–N Atropisomer Synthesis via Electrolyte- and Base-Free Electrochemical Cobalt-Catalysed C–H Annulation
Actions

Comments

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.