Ruthenium(II)‐NNN‐Pincer‐Complex‐Catalyzed Reactions Between Various Alcohols and Amines for Sustainable C−N and C−C Bond Formation

An air and moisture stable 2‐hydroxypyridine based bifunctional ruthenium NNN‐pincer complex catalyzed efficient (TON=42840) N‐alkylation of amines under mild conditions. Surprisingly, with cyclic secondary amines this methodology selectively produced only amides. Notably, N‐methylation of several a...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2018-02, Vol.360 (4), p.722-729
Main Authors: Maji, Milan, Chakrabarti, Kaushik, Paul, Bhaskar, Roy, Bivas Chandra, Kundu, Sabuj
Format: Article
Language:English
Subjects:
2-alkylaminoquinoline
Acceptorless dehydrogenative annulation
Alcohol
Alcohols
Aliphatic compounds
Alkylation
Amides
Amines
bifunctional catalyst
Chemical reactions
Chemical synthesis
Methylation
N-methylation
Nitriles
Organic compounds
quinoline
Reaction time
Ruthenium
Ruthenium compounds
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Summary:An air and moisture stable 2‐hydroxypyridine based bifunctional ruthenium NNN‐pincer complex catalyzed efficient (TON=42840) N‐alkylation of amines under mild conditions. Surprisingly, with cyclic secondary amines this methodology selectively produced only amides. Notably, N‐methylation of several amines was achieved by using methanol as a green methylating agent. Furthermore, with lower catalyst loading (0.2 mol%) and shorter reaction time (6 h) numerous substituted quinolines were synthesized from 2‐aminobenzyl alcohols and secondary alcohols. The effectiveness of this protocol was further extended by successfully synthesizing 2‐alkylaminoquinolines in a one‐pot fashion from amino alcohol, aliphatic nitriles, and alcohols. Gram scale synthesis of various compounds was also investigated to demonstrate the synthetic applicability of this methodology.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201701117