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Issue 10, 2018
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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

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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

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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

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