Vanadium-catalysed regioselective hydroboration of epoxides for synthesis of secondary alcohols

Zhang, Guoqi; Zeng, Haisu; Tang, Quan; Ates, Selin; Zheng, Shengping; Neary, Michelle C.

doi:10.1039/d3dt01865b

Cited by 2 publications

(1 citation statement)

References 34 publications

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“…Traditional protocols for the reduction of epoxides to alcohols, employed strong hydride donor reagents which suffered from poor regioselectivity and led to the generation of stoichiometric salt wastes. [22] During the past years, few transition metal mediated hydrogenation, [23][24][25][26] hydroborylation [27,28] and hydrosilylation [29,30] based strategies were emerged for the selective ring opening of epoxides. Recently, Werner et.…”

Section: Introductionmentioning

confidence: 99%

(NHC)Mn(I) complex catalyzed selective transfer hydrogenation of epoxides, azoarenes and nitroarenes utilizing ammonia borane

Kumari,

Roy,

Saha

et al. 2024

Preprint

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Herein, we have reported an effective protocol for the regioselective transfer hydrogenation (TH) of epoxides by utilizing a phosphine-free bis-NHC-Mn(I) complex and ammonia borane. By employing this strategy, aromatic epoxides were selectively converted to primary alcohols whereas secondary alcohols were obtained exclusively from aliphatic epoxides. The protocol was further extended for the TH of azoarenes and nitroarenes to hydrazoarenes and anilines respectively. Notably, a library of substrates with different functional groups were screened which resulted in the corresponding transfer hydrogenated product in good to excellent yields. A series of mechanistic investigations were carried out to understand the catalytic process.

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Section: Introductionmentioning

confidence: 99%

(NHC)Mn(I) complex catalyzed selective transfer hydrogenation of epoxides, azoarenes and nitroarenes utilizing ammonia borane

Kumari,

Roy,

Saha

et al. 2024

Preprint

View full text Add to dashboard Cite

show abstract

(NHC)Mn(I) Complex Catalyzed Selective Transfer Hydrogenation of Epoxides, Azoarenes and Nitroarenes Utilizing Ammonia Borane

Kumari,

Roy,

Ranjan Saha

et al. 2024

ChemCatChem

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Herein, we have reported an effective protocol for the regioselective transfer hydrogenation (TH) of epoxides by utilizing a phosphine‐free bis‐NHC‐Mn(I) complex and ammonia borane. By employing this strategy, aromatic epoxides were selectively converted to primary alcohols whereas secondary alcohols were obtained exclusively from aliphatic epoxides. The protocol was further extended for the TH of azoarenes and nitroarenes to hydrazoarenes and anilines respectively. Notably, a library of substrates with different functional groups were screened which resulted in the corresponding transfer hydrogenated product in good to excellent yields. A series of mechanistic investigations were carried out to understand the catalytic process.

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Vanadium-catalysed regioselective hydroboration of epoxides for synthesis of secondary alcohols

Abstract: Regioselective epoxide ring-opening through hydroboration catalysed by a vanadium(III) dialkyl complex supported by a redox-active terpyridine ligand is reported. Secondary alcohols were obtained in high yields via effective Markovnikov hydroboration...

Cited by 2 publications

References 34 publications

(NHC)Mn(I) complex catalyzed selective transfer hydrogenation of epoxides, azoarenes and nitroarenes utilizing ammonia borane

(NHC)Mn(I) complex catalyzed selective transfer hydrogenation of epoxides, azoarenes and nitroarenes utilizing ammonia borane

(NHC)Mn(I) Complex Catalyzed Selective Transfer Hydrogenation of Epoxides, Azoarenes and Nitroarenes Utilizing Ammonia Borane

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