Cobalt-Catalyzed Asymmetric Hydrogenation of Ketones Enabled by the Synergism of an N–H Functionality and a Redox-Active Ligand DOI
Zeming Wang, Minhao Li, Weiwei Zuo

и другие.

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(38), С. 26416 - 26426

Опубликована: Сен. 16, 2024

The transition metal-catalyzed asymmetric hydrogenation (AH) of ketones to produce enantioenriched alcohols is an important reaction in organic chemistry with applications the pharmaceutical and agrochemical fields. Using earth-abundant, biorelevant cobalt as central metal catalyst has a high potential improve sustainability achieve reactions that are scalable. However, due d-electron count, designing catalysts exhibit turnover numbers (TONs, ≥1000) enantioselectivities (≥90%) sufficient for synthetic utility practical scalability (≥1 kg scale) remains challenge. In this work, efficient design strategy utilizing amino(imino)diphosphine Co(II) bromide precatalyst presented goal. quantitative production wide range secondary chiral TONs up 150,000 enantiomeric excess (e.e.) 99% at scale 1.35 was achieved, indicating proposed highly promising AH scale-up reactions. A mechanistic study revealed synergism N-H functionality redox-active ligand endows productivity excellent enantioselectivity.

Язык: Английский

Electrochemical regioselective reduction of α-keto amide with methanol as hydrogen source DOI
Jin Zhang, Jilin Wang,

Ya-Hui Sang

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

An electrochemical synthesis of α-hydroxy amides has been developed via the regioselective hydrogenation reduction α-keto amides.

Язык: Английский

Процитировано

0
Cobalt-Catalyzed Asymmetric Hydrogenation of Ketones Enabled by the Synergism of an N–H Functionality and a Redox-Active Ligand DOI
Zeming Wang, Minhao Li, Weiwei Zuo

и другие.

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(38), С. 26416 - 26426

Опубликована: Сен. 16, 2024

The transition metal-catalyzed asymmetric hydrogenation (AH) of ketones to produce enantioenriched alcohols is an important reaction in organic chemistry with applications the pharmaceutical and agrochemical fields. Using earth-abundant, biorelevant cobalt as central metal catalyst has a high potential improve sustainability achieve reactions that are scalable. However, due d-electron count, designing catalysts exhibit turnover numbers (TONs, ≥1000) enantioselectivities (≥90%) sufficient for synthetic utility practical scalability (≥1 kg scale) remains challenge. In this work, efficient design strategy utilizing amino(imino)diphosphine Co(II) bromide precatalyst presented goal. quantitative production wide range secondary chiral TONs up 150,000 enantiomeric excess (e.e.) 99% at scale 1.35 was achieved, indicating proposed highly promising AH scale-up reactions. A mechanistic study revealed synergism N-H functionality redox-active ligand endows productivity excellent enantioselectivity.

Язык: Английский

Процитировано

2