Selective Terminal Functionalization of Linear Alkanes.

Authors :: Bruffaerts J
Kesten I
Buhnik-Rosenblau K
Cohen A
Edri N
Cormier M
Zhang Y
Ho GM
Massad I
Halfon-Verner H
Kashi Y
Marek I
Source :: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2023 Jul 24; Vol. 62 (30), pp. e202306343. Date of Electronic Publication: 2023 Jun 15.
Publication Year :: 2023
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.<br /> (© 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.)