Site-selective amination and/or nitrilation via metal-free C(sp2)–C(sp3) cleavage of benzylic and allylic alcohols

Raghunath Reddy Anugu; John R. Falck

doi:10.1039/D2SC00758D

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

Site-selective amination and/or nitrilation via metal-free C(sp²)–C(sp³) cleavage of benzylic and allylic alcohols†

Raghunath Reddy Anugu

*^a and John R. Falck

Author affiliations

* Corresponding authors

^a Chemistry Division, Biochemistry Dept., Pharmacology Dept., University of Texas Southwestern Medical Center, Dallas, TX 75390, USA
E-mail: anugu.raghunathreddy@utsouthwestern.edu

Abstract

Benzylic/allylic alcohols are converted via site-selective C(sp²)–C(sp³) cleavage to value-added nitrogenous motifs, viz., anilines and/or nitriles as well as N-heterocycles, utilizing commercial hydroxylamine-O-sulfonic acid (HOSA) and Et₃N in an operationally simple, one-pot process. Notably, cyclic benzylic/allylic alcohols undergo bis-functionalization with attendant increases in architectural complexity and step-economy.

Download options Please wait...

Supplementary files

Supplementary information PDF (14977K)

Article information

DOI: https://doi.org/10.1039/D2SC00758D
Article type: Edge Article
Submitted: 07 Feb 2022
Accepted: 04 Apr 2022
First published: 05 Apr 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry

Download Citation

Chem. Sci., 2022,13, 4821-4827

Permissions

Request permissions

Site-selective amination and/or nitrilation via metal-free C(sp²)–C(sp³) cleavage of benzylic and allylic alcohols

R. R. Anugu and J. R. Falck, Chem. Sci., 2022, 13, 4821 DOI: 10.1039/D2SC00758D

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party commercial publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Social activity

Fetching data from CrossRef.
This may take some time to load.

Chemical Science