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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.

Preparation of Alkynes: Dehydrohalogenation

Preparation of Alkynes: Dehydrohalogenation

Introduction
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.

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.

Electrophilic Addition to Alkynes: Halogenation

Electrophilic Addition to Alkynes: Halogenation

Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.

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 Alkenes: Asymmetric Catalytic Hydrogenation

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...

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C-H Xanthylation: A Synthetic Platform for Alkane Functionalization.

William L Czaplyski¹, Christina G Na¹, Erik J Alexanian¹

¹Department of Chemistry, The University of North Carolina at Chapel Hill , Chapel Hill, North Carolina 27599, United States.

Journal of the American Chemical Society

|October 15, 2016

Summary

This study introduces a new C-H functionalization method using N-xanthylamide and blue LEDs. This breakthrough expands accessible chemical structures for complex molecule synthesis and late-stage derivatization.

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Published on: September 18, 2016

Area of Science:

Organic Chemistry
Synthetic Chemistry
Catalysis

Background:

Intermolecular functionalization of aliphatic C-H bonds is crucial for synthesizing complex molecules.
Current C-H functionalization methods have limitations in the accessible chemical space.

Purpose of the Study:

To develop a novel C-H functionalization method that expands the range of accessible chemotypes.
To enable efficient late-stage derivatization of complex molecules.

Main Methods:

Utilizing blue light-emitting diodes (LEDs) for C-H xanthylation.
Employing an easily prepared N-xanthylamide as a key reagent.
Investigating the reaction under conditions where the substrate is the limiting reagent.

Main Results:

Achieved useful chemical yields for C-H xanthylation.
Demonstrated high site selectivity in late-stage functionalizations of complex molecules.
Showcased tolerance of a variety of common functional groups within the reaction.

Conclusions:

The developed C-H xanthylation method significantly broadens the scope of accessible C-H transformations.
The xanthate functional group's versatility is leveraged through polar and radical pathways.
This approach unlocks previously inaccessible synthetic routes for complex molecules.