Ortho -Amino group functionalized 2,2′-bipyridine based Ru(II) complex catalysed alkylation of secondary alcohols, nitriles and amines using alcohols

Bivas Chandra Roy; Subhankar Debnath; Kaushik Chakrabarti; Bhaskar Paul; Milan Maji; Sabuj Kundu

doi:10.1039/c7qo01061c

Ortho -Amino group functionalized 2,2′-bipyridine based Ru(II) complex catalysed alkylation of secondary alcohols, nitriles and amines using alcohols

Bivas Chandra Roy, Subhankar Debnath, Kaushik Chakrabarti, Bhaskar Paul, Milan Maji, Sabuj Kundu^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

80 Scopus citations

Abstract

Various Ru(ii) complexes bearing functionalized 2,2′-bipyridine ligands were synthesized and fully characterized. Among them, a new N6,N6′-dimethyl-2,2′-bipyridine-6,6′-diamine ligand was found to be the most electron-rich ligand as its corresponding Ru(ii) complex (1a) displayed the lowest ν_co value and the highest efficiency in the β-alkylation of secondary alcohols with primary alcohols (TON = 98860). Complex 1a also exhibited a greater reactivity in the monoalkylation of acetonitrile, α-alkylation as well as α-methylation of arylacetonitriles. Compared to the other reported systems, in α-methylation of nitriles complex 1a presented superior catalytic activity. The potential of complex 1a was extended further in N-methylation of amines using methanol as a green methylating agent.

Original language	English
Pages (from-to)	1008-1018
Number of pages	11
Journal	Organic Chemistry Frontiers
Volume	5
Issue number	6
DOIs	https://doi.org/10.1039/c7qo01061c
State	Published - 21 Mar 2018
Externally published	Yes

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Publisher Copyright:
© the Partner Organisations 2018.

ASJC Scopus subject areas

Organic Chemistry

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@article{c40c503641894ad19c976f5a23cd02ca,

title = "Ortho -Amino group functionalized 2,2′-bipyridine based Ru(II) complex catalysed alkylation of secondary alcohols, nitriles and amines using alcohols",

abstract = "Various Ru(ii) complexes bearing functionalized 2,2′-bipyridine ligands were synthesized and fully characterized. Among them, a new N6,N6′-dimethyl-2,2′-bipyridine-6,6′-diamine ligand was found to be the most electron-rich ligand as its corresponding Ru(ii) complex (1a) displayed the lowest νco value and the highest efficiency in the β-alkylation of secondary alcohols with primary alcohols (TON = 98860). Complex 1a also exhibited a greater reactivity in the monoalkylation of acetonitrile, α-alkylation as well as α-methylation of arylacetonitriles. Compared to the other reported systems, in α-methylation of nitriles complex 1a presented superior catalytic activity. The potential of complex 1a was extended further in N-methylation of amines using methanol as a green methylating agent.",

author = "Roy, \{Bivas Chandra\} and Subhankar Debnath and Kaushik Chakrabarti and Bhaskar Paul and Milan Maji and Sabuj Kundu",

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year = "2018",

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doi = "10.1039/c7qo01061c",

language = "English",

volume = "5",

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TY - JOUR

T1 - Ortho -Amino group functionalized 2,2′-bipyridine based Ru(II) complex catalysed alkylation of secondary alcohols, nitriles and amines using alcohols

AU - Roy, Bivas Chandra

AU - Debnath, Subhankar

AU - Chakrabarti, Kaushik

AU - Paul, Bhaskar

AU - Maji, Milan

AU - Kundu, Sabuj

PY - 2018/3/21

Y1 - 2018/3/21

N2 - Various Ru(ii) complexes bearing functionalized 2,2′-bipyridine ligands were synthesized and fully characterized. Among them, a new N6,N6′-dimethyl-2,2′-bipyridine-6,6′-diamine ligand was found to be the most electron-rich ligand as its corresponding Ru(ii) complex (1a) displayed the lowest νco value and the highest efficiency in the β-alkylation of secondary alcohols with primary alcohols (TON = 98860). Complex 1a also exhibited a greater reactivity in the monoalkylation of acetonitrile, α-alkylation as well as α-methylation of arylacetonitriles. Compared to the other reported systems, in α-methylation of nitriles complex 1a presented superior catalytic activity. The potential of complex 1a was extended further in N-methylation of amines using methanol as a green methylating agent.

AB - Various Ru(ii) complexes bearing functionalized 2,2′-bipyridine ligands were synthesized and fully characterized. Among them, a new N6,N6′-dimethyl-2,2′-bipyridine-6,6′-diamine ligand was found to be the most electron-rich ligand as its corresponding Ru(ii) complex (1a) displayed the lowest νco value and the highest efficiency in the β-alkylation of secondary alcohols with primary alcohols (TON = 98860). Complex 1a also exhibited a greater reactivity in the monoalkylation of acetonitrile, α-alkylation as well as α-methylation of arylacetonitriles. Compared to the other reported systems, in α-methylation of nitriles complex 1a presented superior catalytic activity. The potential of complex 1a was extended further in N-methylation of amines using methanol as a green methylating agent.

UR - https://www.scopus.com/pages/publications/85043776526

U2 - 10.1039/c7qo01061c

DO - 10.1039/c7qo01061c

M3 - Article

AN - SCOPUS:85043776526

SN - 2052-4110

VL - 5

SP - 1008

EP - 1018

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

IS - 6

ER -

Ortho -Amino group functionalized 2,2′-bipyridine based Ru(II) complex catalysed alkylation of secondary alcohols, nitriles and amines using alcohols

Abstract

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