Selective Terminal Functionalization of Linear Alkanes**

Jeffrey Bruffaerts; Inbar Kesten; Keren Buhnik-Rosenblau; Anthony Cohen; Nurit Edri; Morgan Cormier; Yuanfei Zhang; Guo Ming Ho; Itai Massad; Hila Halfon-Verner; Yechezkel Kashi; Ilan Marek

doi:10.1002/anie.202306343

Selective Terminal Functionalization of Linear Alkanes**

Jeffrey Bruffaerts, Inbar Kesten, Keren Buhnik-Rosenblau, Anthony Cohen, Nurit Edri, Morgan Cormier, Yuanfei Zhang, Guo Ming Ho, Itai Massad, Hila Halfon-Verner, Yechezkel Kashi, Ilan Marek

Technion - Israel Institute of Technology

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Article number	e202306343
Journal	Angewandte Chemie - International Edition
Volume	62
Issue number	30
DOIs	https://doi.org/10.1002/anie.202306343
State	Published - 24 Jul 2023

Keywords

Alkanes
Biocatalysis
C−H Activation
Metal-Walk
Synthetic Methods

All Science Journal Classification (ASJC) codes

General Chemistry
Catalysis

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10.1002/anie.202306343

Cite this

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title = "Selective Terminal Functionalization of Linear Alkanes**",

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",

author = "Jeffrey Bruffaerts and Inbar Kesten and Keren Buhnik-Rosenblau and Anthony Cohen and Nurit Edri and Morgan Cormier and Yuanfei Zhang and Ho, \{Guo Ming\} and Itai Massad and Hila Halfon-Verner and Yechezkel Kashi and Ilan Marek",

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year = "2023",

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doi = "10.1002/anie.202306343",

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T1 - Selective Terminal Functionalization of Linear Alkanes**

AU - Bruffaerts, Jeffrey

AU - Kesten, Inbar

AU - Buhnik-Rosenblau, Keren

AU - Cohen, Anthony

AU - Edri, Nurit

AU - Cormier, Morgan

AU - Zhang, Yuanfei

AU - Ho, Guo Ming

AU - Massad, Itai

AU - Halfon-Verner, Hila

AU - Kashi, Yechezkel

AU - Marek, Ilan

PY - 2023/7/24

Y1 - 2023/7/24

N2 - 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.

AB - 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.

KW - Alkanes

KW - Biocatalysis

KW - C−H Activation

KW - Metal-Walk

KW - Synthetic Methods

UR - http://www.scopus.com/inward/record.url?scp=85161849420&partnerID=8YFLogxK

U2 - 10.1002/anie.202306343

DO - 10.1002/anie.202306343

M3 - مقالة

SN - 1433-7851

VL - 62

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 30

M1 - e202306343

ER -

Selective Terminal Functionalization of Linear Alkanes**

Abstract

Keywords

All Science Journal Classification (ASJC) codes

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