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Ruthenium(II)‐NNN‐Pincer‐Complex‐Catalyzed Reactions Between Various Alcohols and Amines for Sustainable C−N and C−C Bond Formation
Author(s) -
Maji Milan,
Chakrabarti Kaushik,
Paul Bhaskar,
Roy Bivas Chandra,
Kundu Sabuj
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201701117
Subject(s) - chemistry , pincer movement , ruthenium , catalysis , bifunctional , alkylation , methanol , organic chemistry , alcohol , primary (astronomy) , combinatorial chemistry , dehydrogenation , medicinal chemistry , physics , astronomy
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.