Borrowing hydrogen and dehydrogenative/oxidative cyclization reactions catalyzed by a CCC-NHC pincer Re complex: An air stable catalyst for the synthesis of α-alkylated ketones and quinolines

Pham, Hoang H.; Hollis, T. Keith

doi:10.1016/j.tetlet.2023.154569

Tetrahedron Letters

2023

DOI: 10.1016/j.tetlet.2023.154569

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Borrowing hydrogen and dehydrogenative/oxidative cyclization reactions catalyzed by a CCC-NHC pincer Re complex: An air stable catalyst for the synthesis of α-alkylated ketones and quinolines

Hoang H. Pham

T. Keith Hollis

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2024

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Cited by 3 publications

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Investigations on Superbase Mediated Reactivity of N‐Tosylhydrazones with Aza‐ortho‐Quinone Methide Precursors

P.,

T. K.,

Sebastian

et al. 2024

Eur J Org Chem

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We have encountered a superbase‐mediated chemoselective reaction of N‐tosylhydrazones with aza‐ortho‐quinone methide precursors. When tosylhydrazone was treated with ortho‐aminobenzyl alcohol in super basic conditions (KOH+DMSO), we observed the formation of 2‐substituted quinoline. The reaction was found to be general, and by this method, mono‐, di‐ and tri‐substituted quinolines could be made. We could prove experimentally and theoretically that the reaction proceeded via the formation of an azine from the basic decomposition of N‐tosylhydrazones. Finally, the reaction of tosylhydrazone with N‐(2‐(chloromethyl) phenyl)‐4‐methylbenzenesulfonamide (aza‐ortho‐quinone methide precursor) under super basic conditions afforded hydrazine substituted sulfonamides.

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Investigations on Superbase Mediated Reactivity of N‐Tosylhydrazones with Aza‐ortho‐Quinone Methide Precursors

P.,

T. K.,

Sebastian

et al. 2024

Eur J Org Chem

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Synthesis of a CCC-NHC pincer Mn complex: An earth abundant catalyst for synthesis of α-alkylated ketones, 2-oxindole derivatives via borrowing hydrogen and one-pot synthesis of quinolines

Pham,

Nguyen,

Donnadieu

et al. 2024

Tetrahedron

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Quinoline-derived NNP-manganese complex catalyzed α-alkylation of ketones with primary alcohols

Song,

Rong,

Meng

et al. 2024

Org. Biomol. Chem.

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Borrowing hydrogen and dehydrogenative/oxidative cyclization reactions catalyzed by a CCC-NHC pincer Re complex: An air stable catalyst for the synthesis of α-alkylated ketones and quinolines

Cited by 3 publications

References 64 publications

Investigations on Superbase Mediated Reactivity of N‐Tosylhydrazones with Aza‐ortho‐Quinone Methide Precursors

Investigations on Superbase Mediated Reactivity of N‐Tosylhydrazones with Aza‐ortho‐Quinone Methide Precursors

Synthesis of a CCC-NHC pincer Mn complex: An earth abundant catalyst for synthesis of α-alkylated ketones, 2-oxindole derivatives via borrowing hydrogen and one-pot synthesis of quinolines

Quinoline-derived NNP-manganese complex catalyzed α-alkylation of ketones with primary alcohols

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