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Regioselectivity and Stereochemistry of Hydroboration

Regioselectivity and Stereochemistry of Hydroboration

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...

Hydroboration-Oxidation of Alkenes

Hydroboration-Oxidation of Alkenes

In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.

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...

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...

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Aluminium complexes: next-generation catalysts for selective hydroboration.

Amrita Das¹, Supriya Rej², Tarun K Panda³

¹Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan. amrita.das@chem.eng.osaka-u.ac.jp.

Dalton Transactions (Cambridge, England : 2003)

|February 2, 2022

Summary

This summary is machine-generated.

Aluminium complexes are emerging as efficient catalysts for hydroboration reactions, offering a sustainable alternative to traditional transition metals. These catalysts enable valuable organoborane synthons for diverse chemical transformations.

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Area of Science:

Organometallic Chemistry
Catalysis
Synthetic Organic Chemistry

Background:

Organoboranes are key intermediates in organic synthesis, derived from hydroboration reactions.
Transition metals have historically catalyzed these transformations, but concerns exist regarding toxicity and cost.
Main group metals, particularly aluminum, are gaining attention as sustainable catalysts.

Purpose of the Study:

To explore the potential of aluminum complexes as catalysts in hydroboration reactions.
To develop more efficient and robust catalytic systems for synthesizing organoboranes.
To advance the use of earth-abundant metals in catalysis.

Main Methods:

Hydroboration of alkenes and alkynes using aluminum-based catalysts.
Characterization of resulting organoborane products.
Optimization of reaction conditions for improved yield and selectivity.

Main Results:

Demonstration of aluminum complexes as effective catalysts for hydroboration.
Generation of valuable organoborane synthons suitable for further functionalization.
Comparison of catalytic activity and efficiency with traditional metal catalysts.

Conclusions:

Aluminum complexes represent a promising class of catalysts for hydroboration chemistry.
These catalysts offer a sustainable and efficient route to important organoborane intermediates.
Further development of aluminum-based catalysts can lead to greener synthetic methodologies.