C-C bond cleavage of 1,3-diols by rhenium and iron complexes

Abstract

Lignin is a complex natural biopolymer. It is believed that it may be a potential source of energy and carbon based materials for organic synthesis due to its abundance in plants. In order to fully utilize lignin, it is necessary to depolymerize it into smaller molecules. Lignin contains a major subunit 1,3-diol bonded to aromatic rings. To develop methodology to depolymerize lignin, we studied how to cleave 1,3-diols catalytically. An efficient catalytic system for cleaving the C-C bond in 1,3-diols mediated by ReOCL₃(SMe₂)(OPPh₃) was developed. Heating the substrates at 100 °C in the presence of 5 mol% of ReOCL₃(SMe₂)(OPPh₃) in toluene will give aldehydes and olefins as products. Trans olefins are selectively formed in the reactions. FeCl₃ was also found to be an efficient catalyst for the reaction. Heating 1,3-diols at 100 °C in the presence of 5 mol% of FeCl₃ in toluene can cleave the C-C bonds in 1,3-diols.

Date of Award	2018
Original language	English
Awarding Institution	The Hong Kong University of Science and Technology