Bifunctional RuII-Complex-Catalysed Tandem C−C Bond Formation: Efficient and Atom Economical Strategy for the Utilisation of Alcohols as Alkylating Agents

Bivas Chandra Roy; Kaushik Chakrabarti; Sujan Shee; Subhadeep Paul; Sabuj Kundu

doi:10.1002/chem.201603557

Bifunctional Ru^II-Complex-Catalysed Tandem C−C Bond Formation: Efficient and Atom Economical Strategy for the Utilisation of Alcohols as Alkylating Agents

Bivas Chandra Roy
, Kaushik Chakrabarti
, Sujan Shee
, Subhadeep Paul
, Sabuj Kundu^*

^*Corresponding author for this work

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

65 Scopus citations

Abstract

Catalytic activities of a series of functional bipyridine-based Ru^II complexes in β-alkylation of secondary alcohols using primary alcohols were investigated. Bifunctional Ru^II complex (3 a) bearing 6,6’-dihydroxy-2,2’-bipyridine (6DHBP) ligand exhibited the highest catalytic activity for this reaction. Using significantly lower catalyst loading (0.1 mol %) dehydrogenative carbon−carbon bond formation between numerous aromatic, aliphatic and heteroatom substituted alcohols were achieved with high selectivity. Notably, for the synthesis of β-alkylated secondary alcohols this protocol is a rare one-pot strategy using a metal–ligand cooperative Ru^II system. Remarkably, complex 3 a demonstrated the highest reactivity compared to all the reported transition metal complexes in this reaction.

Original language	English
Pages (from-to)	18147-18155
Number of pages	9
Journal	Chemistry - A European Journal
Volume	22
Issue number	50
DOIs	https://doi.org/10.1002/chem.201603557
State	Published - 12 Dec 2016
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

C−C bond formation
atom economical
bifunctional catalysis
catalysis
ruthenium

ASJC Scopus subject areas

Catalysis
General Chemistry
Organic Chemistry

Access to Document

10.1002/chem.201603557

Cite this

@article{71b66bcfafdb44e0bf4f1cc6a4bf12fd,

title = "Bifunctional RuII-Complex-Catalysed Tandem C−C Bond Formation: Efficient and Atom Economical Strategy for the Utilisation of Alcohols as Alkylating Agents",

abstract = "Catalytic activities of a series of functional bipyridine-based RuII complexes in β-alkylation of secondary alcohols using primary alcohols were investigated. Bifunctional RuII complex (3 a) bearing 6,6{\textquoteright}-dihydroxy-2,2{\textquoteright}-bipyridine (6DHBP) ligand exhibited the highest catalytic activity for this reaction. Using significantly lower catalyst loading (0.1 mol \%) dehydrogenative carbon−carbon bond formation between numerous aromatic, aliphatic and heteroatom substituted alcohols were achieved with high selectivity. Notably, for the synthesis of β-alkylated secondary alcohols this protocol is a rare one-pot strategy using a metal–ligand cooperative RuII system. Remarkably, complex 3 a demonstrated the highest reactivity compared to all the reported transition metal complexes in this reaction.",

keywords = "C−C bond formation, atom economical, bifunctional catalysis, catalysis, ruthenium",

author = "Roy, \{Bivas Chandra\} and Kaushik Chakrabarti and Sujan Shee and Subhadeep Paul and Sabuj Kundu",

note = "Publisher Copyright: {\textcopyright} 2016 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim",

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doi = "10.1002/chem.201603557",

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T1 - Bifunctional RuII-Complex-Catalysed Tandem C−C Bond Formation

T2 - Efficient and Atom Economical Strategy for the Utilisation of Alcohols as Alkylating Agents

AU - Roy, Bivas Chandra

AU - Chakrabarti, Kaushik

AU - Shee, Sujan

AU - Paul, Subhadeep

AU - Kundu, Sabuj

PY - 2016/12/12

Y1 - 2016/12/12

N2 - Catalytic activities of a series of functional bipyridine-based RuII complexes in β-alkylation of secondary alcohols using primary alcohols were investigated. Bifunctional RuII complex (3 a) bearing 6,6’-dihydroxy-2,2’-bipyridine (6DHBP) ligand exhibited the highest catalytic activity for this reaction. Using significantly lower catalyst loading (0.1 mol %) dehydrogenative carbon−carbon bond formation between numerous aromatic, aliphatic and heteroatom substituted alcohols were achieved with high selectivity. Notably, for the synthesis of β-alkylated secondary alcohols this protocol is a rare one-pot strategy using a metal–ligand cooperative RuII system. Remarkably, complex 3 a demonstrated the highest reactivity compared to all the reported transition metal complexes in this reaction.

AB - Catalytic activities of a series of functional bipyridine-based RuII complexes in β-alkylation of secondary alcohols using primary alcohols were investigated. Bifunctional RuII complex (3 a) bearing 6,6’-dihydroxy-2,2’-bipyridine (6DHBP) ligand exhibited the highest catalytic activity for this reaction. Using significantly lower catalyst loading (0.1 mol %) dehydrogenative carbon−carbon bond formation between numerous aromatic, aliphatic and heteroatom substituted alcohols were achieved with high selectivity. Notably, for the synthesis of β-alkylated secondary alcohols this protocol is a rare one-pot strategy using a metal–ligand cooperative RuII system. Remarkably, complex 3 a demonstrated the highest reactivity compared to all the reported transition metal complexes in this reaction.

KW - C−C bond formation

KW - atom economical

KW - bifunctional catalysis

KW - catalysis

KW - ruthenium

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U2 - 10.1002/chem.201603557

DO - 10.1002/chem.201603557

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