Conventional methods for synthesis of functional derivatives of abundant, sustainable, natural polysaccharides are limited in scope, due to their harsh conditions and the low reactivity of many polysaccharide functional groups. As a result only cellulose derivatives have strong commercial importance, and among them only ca. a half-dozen ester types and ca. a half-dozen ether types are commonly made and used. More flexible, facile, and mild chemistries are needed to enhance utilization of these benign, abundant polymers that nature gives us, by greatly enhancing the available structural, functional, and property palettes available to the material designer. We report herein on our progress in developing olefin cross-metathesis, optionally integrated with thiol-Michael addition, as a rapid, mild, flexible, efficient method for synthesis of polysaccharide derivatives with novel and diverse functionality. We will show that the methodology is suited for appending large, sensitive moieties to polysaccharides that would otherwise be difficult or impossible to attach. We will showcase the practical and versatile nature of these chemistries as applied to polysaccharide, and the ways in which we have avoided the potentially damaging side reaction of olefin self-metathesis.

Expanding the arsenal of sustainable polysaccharide derivatives via click (thiol-Michael) and click-like (olefin cross-metathesis) reactions

254th National Meeting (2017)

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