Selective Terminal Functionalization of Linear Alkanes
Jeffrey Bruffaerts1, Inbar Kesten2, Keren Buhnik-Rosenblau2
1Schulich Faculty of Chemistry and the Resnick Sustainability Center for Catalysis. Technion-Israel Institute of Technology, Haifa, 32000, Israel.
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.
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