Redox-neutral organocatalytic Mitsunobu reactions

Nucleophilic substitution reactions of alcohols are among the most fundamental and strategically important transformations in organic chemistry. For over half a century, these reactions have been achieved by using stoichiometric, and often hazardous, reagents to activate the otherwise unreactive alcohols. Here, we demonstrate that a specially designed phosphine oxide promotes nucleophilic substitution reactions of primary and secondary alcohols in a redox-neutral catalysis manifold that produces water as the sole by-product. The scope of the catalytic coupling process encompasses a range of acidic pronucleophiles that allow stereospecific construction of carbon-oxygen and carbon-nitrogen bonds.

Source: ScienceNOW - August 28, 2019 Category: Science Authors: Beddoe, R. H., Andrews, K. G., Magne, V., Cuthbertson, J. D., Saska, J., Shannon-Little, A. L., Shanahan, S. E., Sneddon, H. F., Denton, R. M. Tags: Chemistry reports Source Type: news