B(C6F5)3-catalyzed dehydrogenative cyclization of N-tosylhydrazones and anilines via a Lewis adduct: a combined experimental and computational investigation

Murali Mohan Guru; Sriman De; Sayan Dutta; Debasis Koley; Biplab Maji

doi:10.1039/C9SC02492A

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

B(C₆F₅)₃-catalyzed dehydrogenative cyclization of N-tosylhydrazones and anilines via a Lewis adduct: a combined experimental and computational investigation†

Murali Mohan Guru,

‡^a Sriman De,

‡^a Sayan Dutta,

^a Debasis Koley

*^a and Biplab Maji

*^a

Author affiliations

* Corresponding authors

^a Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur-741246, India
E-mail: koley@iiserkol.ac.in, bm@iiserkol.ac.in

Abstract

Tris(pentafluorophenyl)borane-catalyzed dehydrogenative-cyclization of N-tosylhydrazones with aromatic amines has been disclosed. This metal-free catalytic protocol is compatible with a range of functional groups to provide both symmetrical and unsymmetrical 3,4,5-triaryl-1,2,4-triazoles. Mechanistic experiments and density functional theory (DFT) studies suggest an initial Lewis adduct formation of N-tosylhydrazone with B(C₆F₅)₃ followed by sequential intermolecular amination of the borane adduct with aniline, intramolecular cyclization and frustrated Lewis pair (FLP)-catalyzed dehydrogenation for the generation of substituted 1,2,4-triazoles.

This article is part of the themed collection: Celebrating the Chemical Sciences in India - Leaders in the Field Symposium 2020

Download options Please wait...

Supplementary files

Article information

DOI: https://doi.org/10.1039/C9SC02492A
Article type: Edge Article
Submitted: 22 May 2019
Accepted: 05 Jul 2019
First published: 05 Jul 2019
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., 2019,10, 7964-7974

Permissions

Request permissions

B(C₆F₅)₃-catalyzed dehydrogenative cyclization of N-tosylhydrazones and anilines via a Lewis adduct: a combined experimental and computational investigation

M. M. Guru, S. De, S. Dutta, D. Koley and B. Maji, Chem. Sci., 2019, 10, 7964 DOI: 10.1039/C9SC02492A

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