Retention of palladium and phosphine ligands using nanoporous polydicyclopentadiene thimbles.

Thimbles composed of polydicyclopentadiene retained Pd and phosphines used in Buchwald-Hartwig and Sonogashira coupling reactions but allowed the products to permeate. The products were isolated in high yields on the exteriors of the thimbles with no detectable contamination from phosphine and with Pd loadings as low as < 5.5 ppm.

Scale-up of pseudo solid-phase enzymatic synthesis of alpha-methyl glucoside acrylate.

The successful scale-up of the enzymatic synthesis of alpha-methyl glucoside acrylate from laboratory-scale (milliliter) to pilot-scale (liter) was examined. Specifically, Candida antarctica lipase B (Novozym 435) was used as a biocatalyst to produce alpha-methyl glucoside acrylate via the transesterification of alpha-methyl glucoside (MG) with vinyl acrylate (VA) using acetone as a solvent. This is a pseudo-solid-phase synthesis; only a fraction of the alpha-methyl glucoside and the product are soluble in acetone. Molecular sieves were used to remove traces of water in the reaction medium and to increase enzyme stability by removing the acetaldehyde by-product. A general method was also developed to purify and recover the monoacrylate product from unreacted sugar and undesired diester by a simple crystallization and precipitation process.