Alkylation of amines with allylic alcohols and deep eutectic solvents as metal-free and green catalyst

06 January 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


A novel approach for the allylic alkylation of anilines, hydrazides and indole derivatives by the direct use of allylic alcohols is described under very mild conditions, such as room temperature and using sustainable deep eutectic solvents (DESs). The search of the optimum DES to be used in the reaction reveals that a simple mixture of choline chloride (ChCl) and lactic acid provides excellent results for a wide substrate scope and with high isolated yields. This methodology represents a great improvement compared to other procedures described in literature, for which high temperatures, stronger reaction conditions or metal catalysts are usually required. In some cases, this protocol affords to the first examples of trapping allylic carbocations with indole derivatives. All these features make this procedure an appealing and green alternative in comparison with other examples reported in literature on alkylation of amines by allylic alcohols. Preliminary mechanistic studies using unsymmetrically substituted alcohols support that the reaction should proceed by an SN1 pathway.Introduction.


allylic alcohols
deep eutectic solvents
green catalyst


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.