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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: 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...

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.

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...

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 trans-Alkenes: Sodium in Liquid Ammonia

Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia

Alkynes can be reduced to trans-alkenes using sodium or lithium in liquid ammonia. The reaction, known as dissolving metal reduction, proceeds with an anti addition of hydrogen across the carbon–carbon triple bond to form the trans product. Since ammonia exists as a gas (bp = −33°C) at room temperature, the reaction is carried out at low temperatures using a mixture of dry ice (sublimes at −78°C) and acetone.
When dissolved in liquid ammonia, an alkali metal,...

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Alkenyl Thioetherification Enabled by Nickel Catalysis.

Bing Xu^1,2, Huan Xiang^1,2, Yuqiong Tan^1,2

¹School of Pharmacy, Hangzhou Normal University, Hangzhou, Zhejiang 311121, PR China.

The Journal of Organic Chemistry

|March 28, 2023

Summary

This summary is machine-generated.

This study presents an efficient nickel-catalyzed method for creating alkenyl thioethers from common starting materials. This strategy offers a versatile approach for synthesizing complex molecules, including pharmaceuticals.

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Area of Science:

Organic Chemistry
Catalysis
Synthetic Methodology

Background:

Alkenyl thioethers are important structural motifs in pharmaceuticals and natural products.
Efficient methods for forming alkenyl C(sp2)-S bonds are crucial for synthetic chemists.

Purpose of the Study:

To develop an efficient and broadly applicable method for alkenyl thioetherification.
To utilize nickel catalysis for the cross-coupling of alkenyl halides with thio-alcohols/phenols.

Main Methods:

Nickel-catalyzed cross-coupling reaction.
Utilized inactivated or β-aryl-substituted (E)-alkenyl halides and thio-alcohols/phenols.
Employed mildly basic reaction conditions.

Main Results:

Achieved an efficient strategy for alkenyl thioetherification.
Demonstrated a broad scope of substrates, including protected amino acids, saccharides, and heterocycles.
Successfully applied the method to late-stage modification of complex natural products and pharmaceuticals.

Conclusions:

The developed nickel-catalyzed strategy is a highly effective method for alkenyl C(sp2)-S bond formation.
The mild conditions and broad scope make this method valuable for synthesizing diverse and complex organic molecules.
This approach offers significant utility in medicinal chemistry and natural product synthesis.