A molybdenum-catalyzed acceptorless dehydrogenative approach for quinoline synthesis using amino alcohol

We report the bidentate-phosphine-ligand-based molybdenum π-allyl complex [Mo(CO)<sub>2</sub>(η<sup>3</sup>-C<sub>3</sub>H<sub>5</sub>)(DPPE)Cl] (Mo-1; DPPE = 1,2-bis(diphenylphosphino)ethane) for the dehydrogenative annulation of 2-aminobenzyl alcohol with a wide variety of methylketones to form N-heterocycle quinoline derivatives. The complex Mo-1 also catalyzed the formation of substituted quinolines through the reaction of 2-aminobenzyl alcohol with 1-phenylethanol derivatives. This methodology demands low loading of the complex (1 mol%) and a catalytic base. The process produces water and hydrogen gas as the only byproducts. Thus, the reactions are atom-efficient and environmentally benign.

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Publication Details

Journal
Organic & Biomolecular Chemistry
Published
2025-01-01
DOI
https://doi.org/10.1039/d5ob01409c
Primary Topic
Asymmetric Hydrogenation and Catalysis
Type
article
Field-Weighted Citation Impact
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article

A molybdenum-catalyzed acceptorless dehydrogenative approach for quinoline synthesis using amino alcohol

Debangsu Sil, Vaishnavi Atreya, A. K. SIL, Subrata Chakraborty
Organic & Biomolecular Chemistry
Asymmetric Hydrogenation and Catalysis
article

A molybdenum-catalyzed acceptorless dehydrogenative approach for quinoline synthesis using amino alcohol

Debangsu Sil, Vaishnavi Atreya, A. K. SIL, Subrata Chakraborty
article en

Abstract

We report the bidentate-phosphine-ligand-based molybdenum π-allyl complex [Mo(CO)<sub>2</sub>(η<sup>3</sup>-C<sub>3</sub>H<sub>5</sub>)(DPPE)Cl] (Mo-1; DPPE = 1,2-bis(diphenylphosphino)ethane) for the dehydrogenative annulation of 2-aminobenzyl alcohol with a wide variety of methylketones to form N-heterocycle quinoline derivatives. The complex Mo-1 also catalyzed the formation of substituted quinolines through the reaction of 2-aminobenzyl alcohol with 1-phenylethanol derivatives. This methodology demands low loading of the complex (1 mol%) and a catalytic base. The process produces water and hydrogen gas as the only byproducts. Thus, the reactions are atom-efficient and environmentally benign.

Organic & Biomolecular ChemistryVol. 23(44)
Indian Institute of Technology Jodhpur (IN), Indian Institute of Science Education and Research Pune (IN)
Openalex Percentile: Top 77%
Asymmetric Hydrogenation and Catalysis
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