Epoxides of soybean oil methyl esters (SMEs) are biodegradable, non-toxic, and renewable epoxy plasticizers. The objective of the present work was to investigate the effects of free fatty acids on the enzymatic epoxidation of SMEs. The results showed that the epoxidation of SMEs depended on the type of the added free fatty acid. For saturated ( C 18:0 ) and monounsaturated free fatty acids, the epoxy oxygen group content (EOC) of SMEs increased with increasing carbon chain length of free fatty acids; for branched-chain unsaturated free fatty acids, the EOC of SMEs decreased in the presence of hydroxyl group (OH) and hydroperoxide (OOH) of free fatty acids; the EOC of SMEs decreased with increasing number of double bonds of free fatty acids. The maximum EOC and the initial epoxidization rate (V 0 ) linearly decreased with increasing peroxide value of SMEs. The highest EOC (6.87 AE 0.3%) of SMEs was obtained using behenic acid as reaction material, which was similar with that of stearic acid (EOC 6.75 AE 0.2%).

A visible-light-induced C-5 selective C-H borylation of imidazo[1,2-a]pyridines with NHC-BH 3 via Minisci-type radical borylation reaction has been developed for the first time. The present sustainable protocol provides a new family of regioselectively C5-borylated imidazopyridines that would otherwise be difficult to prepare. It is a supplement to site-selective borylation of azines (nitrogen-containing aromatic heterocycles) and the assembly of sp 2 carbon-boron bond.

An efficient cascade methodology toward chemoselective synthesis of N-fused heterocycles in-indole derivatives has been developed. This transformation proceeds via a silver(I) triflate-catalyzed consecutive FriedelCrafts reaction/N À C bond formation sequence between readily available propargyl alcohols and 3-substituted 1H-indoles. Not only is excellent chemoselectivity observed according to the substitution patterns of propargyl alcohols, but also the Lewis acid-catalyzed N À C bond formation process can be carried out under base-and ligand-free conditions.

A palladium-catalyzed difluoromethylation of a series of aryl chlorides and triflates under mild conditions was described. A variety of common functional groups were tolerated. In addition, by using this protocol, several drug molecules containing an aryl chloride unit were successfully difluoromethylated, thus enabling medicinal chemists to rapidly access novel drug derivatives with potentially improved properties via late-stage functionalization.