Jump to main content
Jump to site search

Issue 10, 2018

A nitrogen-ligated nickel-catalyst enables selective intermolecular cyclisation of β- and γ-amino alcohols with ketones: access to five and six-membered N-heterocycles

Author affiliations

Abstract

Owing to the great demand for the synthesis of N-heterocycles, development of new reactions that utilise renewable resources and convert them into key chemicals using non-precious base metal-catalysts is highly desirable. Herein, we demonstrated a sustainable Ni-catalysed dehydrogenative approach for the synthesis of pyrroles, pyridines, and quinolines by the reaction of β- and γ-amino alcohols with ketones via C–N and C–C bond formations in a tandem fashion. A variety of aryl, hetero-aryl, and alkyl ketones having free amine, halide, alkyl, alkoxy, alkene, activated benzyl, and pyridine moieties were converted into synthetically interesting 2,3 and 2,3,5-substituted bicyclic as well as tricyclic N-heterocycles with up to 90% yields. As a highlight, we demonstrated the synthesis of an interesting pyrrole derivative by intermolecular cyclisation of a steroid hormone with phenylalaninol.

Graphical abstract: A nitrogen-ligated nickel-catalyst enables selective intermolecular cyclisation of β- and γ-amino alcohols with ketones: access to five and six-membered N-heterocycles

Supplementary files

Article information


Submitted
29 Jan 2018
Accepted
03 Apr 2018
First published
04 Apr 2018

Green Chem., 2018,20, 2250-2256
Article type
Paper

A nitrogen-ligated nickel-catalyst enables selective intermolecular cyclisation of β- and γ-amino alcohols with ketones: access to five and six-membered N-heterocycles

K. Singh, M. Vellakkaran and D. Banerjee, Green Chem., 2018, 20, 2250 DOI: 10.1039/C8GC00318A

To request permission to reproduce material from this article, 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 publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.


Social activity

Search articles by author

Spotlight

Advertisements