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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...

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.

Regioselectivity and Stereochemistry of Hydroboration

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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.

Reduction of Alkenes: Catalytic Hydrogenation

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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...

Catalysis

Catalysis

The presence of a catalyst affects the rate of a chemical reaction. A catalyst is a substance that can increase the reaction rate without being consumed during the process. A basic comprehension of a catalysts’ role during chemical reactions can be understood from the concept of reaction mechanisms and energy diagrams.

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.

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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

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Organocatalysis in Inert C-H Bond Functionalization.

Yan Qin^1,2, Lihui Zhu^1,2, Sanzhong Luo^1,2

¹Key Laboratory for Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences , Beijing 100190, China.

Chemical Reviews

|July 13, 2017

Summary

This review summarizes how organocatalysis enhances inert C-H bond functionalization, making reactions more predictable and selective. It covers alkane, arene, and vinyl C-H bonds, plus activated positions, using various organocatalytic modes.

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Area of Science:

Synthetic Chemistry
Catalysis
Organic Chemistry

Background:

Organocatalysis and C-H bond functionalization are rapidly advancing fields.
Combining these areas offers powerful strategies for chemical synthesis.
This synergy enables more efficient and selective transformations of inert chemical bonds.

Purpose of the Study:

To comprehensively review the application of organocatalysis in inert C-H bond functionalization over the last 20 years.
To categorize advancements based on the type of C-H bond being functionalized.
To elucidate the specific organocatalytic modes employed in these transformations.

Main Methods:

Systematic literature review of organocatalysis in C-H functionalization.
Classification of C-H bonds into categories: alkane, arene, vinyl, activated benzylic, allylic, and alpha-heteroatom.
Organization of findings by the explicit organocatalytic mode utilized.

Main Results:

Demonstrated the significant progress and power of combining organocatalysis with C-H functionalization.
Highlighted the increased viability, predictability, and selectivity achieved through this merged approach.
Provided a structured overview of methods targeting diverse C-H bond types.

Conclusions:

Organocatalysis has become a crucial tool for advancing inert C-H bond functionalization.
The integration of organocatalysis offers versatile and efficient synthetic pathways.
Future research directions can be guided by the categorized landscape of organocatalytic C-H functionalization.