Nitrogen Ligated Nickel-Catalyst Enables Selective Intermolecular Cyclisation of β- and γ-Amino Alcohols with Ketones: Access to Five and Six-member N-Heterocycles

Debasis Banarjee, Khushboo Singh, Mari Vellakkaran

Index: 10.1039/C8GC00318A

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Abstract

Owing to the great demand for 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. Here we disclosed a sus-tainable Ni-catalysed dehydrogenative approach for pyrroles, pyridines and quinolines synthesis employing 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, halides, alkyl, alkoxy, alkenes, activated benzyl and pyridine moiety converted into synthetically interesting 2,3 and 2,3,5 substituted bicyclic as well as tricyclic N-heterocycles in up to 90% yields. As a special highlights, we demonstrated an interesting pyrrole derivative employing intermolecular cyclisation of steroid hormone with phenylalaninol.