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Preparation of Alkynes: Alkylation Reaction

Preparation of Alkynes: Alkylation Reaction

Introduction
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.

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
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...

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
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.

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Introduction
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.

Reduction of Alkenes: Catalytic Hydrogenation

Reduction of Alkenes: Catalytic Hydrogenation

Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called 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...

Radical Substitution: Halogenation of Alkanes and Alkyl Substituents

Radical Substitution: Halogenation of Alkanes and Alkyl Substituents

In the presence of heat or light, alkanes react with molecular halogens to form alkyl halides by a substitution reaction called radical halogenation. This reaction has three steps: initiation, propagation, and termination, as seen in the radical chlorination of methane to produce methyl chloride.
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...

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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.

Angewandte Chemie (International Ed. in English)

|May 27, 2023

Summary

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.

Keywords:

Alkanes Biocatalysis C−H Activation Metal-Walk Synthetic Methods

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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.