Phosphine‐Free NNN‐Manganese Complex Catalyzed α‐Alkylation of Ketones with Primary Alcohols and Friedländer Quinoline Synthesis

Herein, we report a very simple and inexpensive catalytic system based on Earth's abundant transition metal manganese and on a bench‐stable phosphine‐free NNN‐pincer ligand for an atom‐efficient α‐alkylations of ketones with primary alcohols via hydrogen‐autotransfer C−C bond formation protocol...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2018-09, Vol.360 (17), p.3233-3238
Main Authors: Barman, Milan K., Jana, Akash, Maji, Biplab
Format: Article
Language:English
Subjects:
Alcohol
Alcohols
Alkylation
Catalysis
Chemical synthesis
Friedländer reaction
Hydrogen-autotransfer
Ketones
Manganese
Manganese catalysts
NNN-pincer
Quinoline
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Summary:Herein, we report a very simple and inexpensive catalytic system based on Earth's abundant transition metal manganese and on a bench‐stable phosphine‐free NNN‐pincer ligand for an atom‐efficient α‐alkylations of ketones with primary alcohols via hydrogen‐autotransfer C−C bond formation protocol. The precatalyst could be generated in situ and could be activated by using catalytic amount of base under milder conditions. A range of ketones were efficiently diversified with a broad range of primary alcohols in good to excellent isolated yields. Remarkably, this catalyst could also be employed for the synthesis of quinoline derivatives using 2‐aminobenzyl alcohol as an alkylating agent. The later reaction is highly benign producing only hydrogen and water as byproducts.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201800380