Selective Terminal Functionalization of Linear Alkanes

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 mu...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2023-07, Vol.62 (30), p.e202306343-n/a
Main Authors: Bruffaerts, Jeffrey, Kesten, Inbar, Buhnik‐Rosenblau, Keren, Cohen, Anthony, Edri, Nurit, Cormier, Morgan, Zhang, Yuanfei, Ho, Guo‐Ming, Massad, Itai, Halfon‐Verner, Hila, Kashi, Yechezkel, Marek, Ilan
Format: Article
Language:English
Subjects:
Alkanes
Alkenes
Biocatalysis
C−H Activation
Dehydrogenation
Metal-Walk
Rhodococcus
Synthetic Methods
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Summary: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. 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 reaction goes through a site‐selective functionalization at the unreactive primary C−H bonds of the linear alkane and avoids the use of linear α‐olefins.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.202306343