Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 19, Issue 33, Pages 7217-7233Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1ob01154e
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Funding
- DST, Government of India [CRG/2019/001737]
- CSIR, Government of India [01(0683)/20]
- Department of Science & Technology and Biotechnology, Government of West Bengal [ST/P/ST/15G-13/2019]
- CSIR
- IIESTS
- DST
- UGC
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In this study, a nickel-catalyzed sustainable synthesis method was utilized to prepare a variety of five-membered fused nitrogen heterocycles, including benzimidazole, purine, benzothiazole, and benzoxazole. This was achieved through acceptorless dehydrogenative functionalization of alcohols and borrowing hydrogen approach, using a bench stable, easy to prepare, and inexpensive Ni(ii)-catalyst. Control experiments were conducted to elucidate the reaction mechanism.
Herein we report nickel-catalyzed sustainable synthesis of a few chosen five-membered fused nitrogen heterocycles such as benzimidazole, purine, benzothiazole, and benzoxazole via acceptorless dehydrogenative functionalization of alcohols. Using a bench stable, easy to prepare, and inexpensive Ni(ii)-catalyst, [Ni(MeTAA)] (1a), featuring a tetraaza macrocyclic ligand (tetramethyltetraaza[14]annulene (MeTAA)), a wide variety of polysubstituted benzimidazole, purine, benzothiazole, and benzoxazole derivatives were prepared via dehydrogenative coupling of alcohols with 1,2-diaminobenzene, 4,5-diaminopyrimidine, 2-aminothiphenol, and 2-aminophenol, respectively. A wide array of benzimidazoles were also prepared via a borrowing hydrogen approach involving alcohols as hydrogen donors and 2-nitroanilines as hydrogen acceptors. A few control experiments were performed to understand the reaction mechanism.
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