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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...

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.

Preparation of Alcohols via Addition Reactions

Preparation of Alcohols via Addition Reactions

Overview
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...

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Related Experiment Video

Updated: Sep 17, 2025

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs

Published on: January 17, 2020

Constructing a multisite catalyst for achieving efficient and highly selective borohydride oxidation reaction.

Liangyao Xue¹, Wenjuan Shi¹, Dian Song²

¹State Key Laboratory of Molecular Engineering of Polymers, Department of Macromolecular Science, Fudan University, Shanghai 200438, China.

Journal of Colloid and Interface Science

|July 1, 2025

Summary

Developing efficient borohydride oxidation reduction (BOR) electrocatalysts is key for direct borohydride fuel cells (DBFCs). This study introduces a novel multisite catalyst, CoFe&AuC, significantly boosting BOR performance and fuel efficiency.

Keywords:

Borohydride oxidation reaction CoFe&AuC DBFC Fuel utilization Multisite catalyst

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Last Updated: Sep 17, 2025

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs

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Published on: January 17, 2020

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

Area of Science:

Electrochemistry
Materials Science
Catalysis

Background:

Direct borohydride fuel cells (DBFCs) require efficient and cost-effective electrocatalysts for borohydride oxidation reduction (BOR).
Existing catalysts often struggle to achieve high BOR rates, Faradaic efficiency, and low onset potentials simultaneously.

Purpose of the Study:

To develop a novel multisite catalyst for enhanced BOR activity and selectivity in DBFCs.
To investigate the synergistic effects of catalyst components on BOR performance.

Main Methods:

Synthesis and characterization of a CoFe&AuC multisite catalyst.
Electrochemical performance testing in DBFCs using air and O2 as oxidants.
In situ spectroscopy and Density Functional Theory (DFT) calculations to elucidate the catalytic mechanism.

Main Results:

The CoFe&AuC catalyst achieved peak power densities of 580 mW/cm² (air oxidant) and 1371 mW/cm² (O2 oxidant).
Performance was significantly higher than control catalysts (CoFe&C and AuC).
High electron transfer number (5.4) and fuel efficiency (65.6%) indicated excellent BOR selectivity.

Conclusions:

The multisite CoFe&AuC catalyst demonstrates superior BOR activity and selectivity due to a tandem effect between CoFe LDH and Au nanoparticles.
This work presents a new strategy for designing high-performance multisite electrocatalysts for DBFCs.