Bifunctional Ru(ii) complex catalysed carbon-carbon bond formation: an eco-friendly hydrogen borrowing strategy.
The atom economical borrowing hydrogen methodology enables the use of alcohols as alkylating agents for selective C-C bond formation. A bifunctional 2-(2-pyridyl-2-ol)-1,10-phenanthroline (phenpy-OH) based Ru(ii) complex (2) was found to be a highly efficient catalyst for the one-pot β-alkylation of secondary alcohols with primary alcohols and double alkylation of cyclopentanol with different primary alcohols. Exploiting the metal-ligand cooperativity in complex 2, several aromatic, aliphatic and heteroatom substituted alcohols were selectively cross-coupled in high yields using significantly low catalyst loading (0.1 mol%). An outer-sphere mechanism is proposed for this system as exogenous PPh3has no significant effect on the rate of the reaction. Notably, this is a rare one-pot strategy for β-alkylation of secondary alcohols using a bifunctional Ru(ii)-complex. Moreover, this atom-economical methodology displayed the highest cumulative turn over frequency (TOF) among all the reported transition metal complexes in cross coupling of alcohols.
Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur 208016, India. sabuj@iitk.ac.in.
Kaushik
K
Chakrabarti
Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur 208016, India. sabuj@iitk.ac.in.
Bhaskar
B
Paul
Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur 208016, India. sabuj@iitk.ac.in.
Milan
M
Maji
Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur 208016, India. sabuj@iitk.ac.in.
Bivas Chandra
BC
Roy
Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur 208016, India. sabuj@iitk.ac.in.
Sujan
S
Shee
Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur 208016, India. sabuj@iitk.ac.in.
Sabuj
S
Kundu