Selective Terminal Functionalization of Linear Alkanes

Angew Chem Int Ed Engl. 2023 Jul 24;62(30):e202306343. doi: 10.1002/anie.202306343. Epub 2023 Jun 15.

Abstract

A two-step sequential strategy involving a biocatalytic dehydrogenation/remote hydrofunctionalization, as a unified and versatile approach to selectively convert linear alkanes into a large array of valuable functionalized aliphatic derivatives is reported. The dehydrogenation is carried out by a mutant strain of a bacteria Rhodococcus and the produced alkenes are subsequently engaged in a remote functionalization through a metal-catalyzed hydrometalation/migration sequence that subsequently react with a large variety of electrophiles. The judicious implementation of this combined biocatalytic and organometallic approach enabled us to develop a high-yielding protocol to site-selectively functionalize unreactive primary C-H bonds.

Keywords: Alkanes; Biocatalysis; C−H Activation; Metal-Walk; Synthetic Methods.