Nickel-Catalyzed Reductive Hydrolysis of Nitriles to Alcohols

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15640%2F25%3A73630826" target="_blank" >RIV/61989592:15640/25:73630826 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/61989100:27640/25:10256268

Výsledek na webu

<a href="https://onlinelibrary.wiley.com/doi/10.1002/anie.202414689" target="_blank" >https://onlinelibrary.wiley.com/doi/10.1002/anie.202414689</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/anie.202414689" target="_blank" >10.1002/anie.202414689</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Nickel-Catalyzed Reductive Hydrolysis of Nitriles to Alcohols

Popis výsledku v původním jazyce

Nitriles are an abundant class of compounds that are widely used as versatile feedstocks to produce various chemicals including pharmaceuticals, and agrochemicals as well as materials. Here we report Ni-catalyzed reductive hydrolysis of nitriles to alcohols in the presence of molecular hydrogen. This conversion likely occurs in a domino reaction sequence that first involves the hydrogenation of nitrile to primary imine, then the hydrolysis of imine, and subsequent deamination to the aldehyde, which is finally hydrogenated to the desired alcohol. Crucial for this reductive hydrolysis process is the commercially available triphos-ligated Ni-complex that enables highly efficient and selective transformation of aromatic, heterocyclic, and aliphatic nitriles including fatty nitriles to prepare functionalized primary alcohols. Further, the synthetic applicability of this Ni-based protocol is presented for the selective conversion of nitrile to alcoholic group in structurally diverse and complex drug molecules as well as agrochemicals. The resulting products, alcohols are indispensable chemicals commonly used in organic synthesis and life sciences as well as material and energy technologies.

Název v anglickém jazyce

Nickel-Catalyzed Reductive Hydrolysis of Nitriles to Alcohols

Popis výsledku anglicky

Nitriles are an abundant class of compounds that are widely used as versatile feedstocks to produce various chemicals including pharmaceuticals, and agrochemicals as well as materials. Here we report Ni-catalyzed reductive hydrolysis of nitriles to alcohols in the presence of molecular hydrogen. This conversion likely occurs in a domino reaction sequence that first involves the hydrogenation of nitrile to primary imine, then the hydrolysis of imine, and subsequent deamination to the aldehyde, which is finally hydrogenated to the desired alcohol. Crucial for this reductive hydrolysis process is the commercially available triphos-ligated Ni-complex that enables highly efficient and selective transformation of aromatic, heterocyclic, and aliphatic nitriles including fatty nitriles to prepare functionalized primary alcohols. Further, the synthetic applicability of this Ni-based protocol is presented for the selective conversion of nitrile to alcoholic group in structurally diverse and complex drug molecules as well as agrochemicals. The resulting products, alcohols are indispensable chemicals commonly used in organic synthesis and life sciences as well as material and energy technologies.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

21001 - Nano-materials (production and properties)

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2025

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

ISSN

1433-7851

e-ISSN

1521-3773

Svazek periodika

64

Číslo periodika v rámci svazku

10

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

8

Strana od-do

nestránkováno

Kód UT WoS článku

001387345100001

EID výsledku v databázi Scopus

2-s2.0-85213799539