Markovnikov Selective Hydroboration of Aryl Alkenes Catalyzed by Quaternary Ammonium Salts

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

Abstract

Despite recent advancements in the development of catalytic Markovnikov-selective hydroboration of alkenes, the metal-free procedure has long remained an unsolved challenge. Here, we report an organocatalytic Markovnikov-selective hy-droboration of aryl alkenes using a commercially available quaternary ammonium catalyst. The method is operationally simple, scalable, and compatible with a wide variety of substrates and it can be successfully applied in the synthesis of active pharmaceutical ingredients (API) such as Chlorphenoxamine. Through in-depth experimental and DFT studies, we elucidate a nuanced understanding of the mechanism and regioselectivity of this reaction.

Keywords

Hydroboration
Catalysis
Alkenes
Markovnikov
Organocatalysis
Ionic Liquid
Quaternary Ammonium Salt

Supplementary materials

Title
Description
Actions
Title
Supplementary Information
Description
Supporting Information
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.