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.
This study presents a novel two-step method using bacteria and metal catalysts to convert alkanes into functionalized derivatives. This approach efficiently targets unreactive C-H bonds, offering a versatile route to valuable chemical compounds.
Area of Science:
- Organic Chemistry
- Biocatalysis
- Organometallic Chemistry
Background:
- Selective functionalization of unreactive C-H bonds in alkanes remains a significant challenge in synthetic chemistry.
- Developing efficient and versatile methods for converting simple alkanes into valuable derivatives is crucial for various industries.
Purpose of the Study:
- To report a unified and versatile two-step sequential strategy for the selective conversion of linear alkanes into functionalized aliphatic derivatives.
- To develop a high-yielding protocol for site-selective functionalization of primary C-H bonds.
Main Methods:
- Biocatalytic dehydrogenation of alkanes using a mutant strain of Rhodococcus bacteria.
- Remote hydrofunctionalization of the produced alkenes via a metal-catalyzed hydrometalation/migration sequence.
- Reaction of the functionalized intermediates with a diverse range of electrophiles.
Main Results:
- Successful conversion of linear alkanes into a wide array of functionalized aliphatic derivatives.
- High yields achieved in the site-selective functionalization of primary C-H bonds.
- Demonstration of a versatile approach combining biocatalysis and organometallic catalysis.
Conclusions:
- The reported two-step strategy offers a powerful and efficient method for alkane functionalization.
- This combined biocatalytic and organometallic approach provides a valuable tool for synthetic chemists.
- The protocol enables the selective transformation of unreactive C-H bonds into useful chemical products.
More Related Videos
05:34Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
Published on: December 16, 2019
10:10Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
Published on: July 28, 2018
Related Concept Videos
02:27Preparation of Alkynes: Alkylation Reaction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
02:17Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
02:47Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
02:24Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
02:13Reduction of Alkenes: Catalytic Hydrogenation
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...
01:27Radical Substitution: Halogenation of Alkanes and Alkyl Substituents
In the initiation step of the reaction, the chlorine molecule undergoes homolytic cleavage in the presence of light or heat, forming two highly reactive chlorine radicals. Propagation occurs in two...