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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.

Ladder Diagrams: Complexation Equilibria

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Ladder diagrams are useful for evaluating equilibria involving metal-ligand complexes. The vertical scale of the ladder diagram represents the concentration of unreacted or free ligand, pL. The horizontal lines on the scale depict the log of stepwise formation constants for metal-ligand complexes and indicate the dominant species in all the regions.
The formation constant, K1, for the formation of Cd(NH3)2+ complex from cadmium and ammonia is 3.55 × 102. Log K1 (i.e. pNH3) is 2.55, and...

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.

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...

Preparation of Alcohols via Addition Reactions

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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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An oxygen-based nucleophile, like water, can undergo addition reactions with aldehydes and ketones. The reaction leads to the formation of hydrates, also referred to as 1,1-diols or geminal diols.
The formation of hydrates is a reversible reaction. Hydrate formation is influenced by steric and electronic factors accompanying the alkyl substituents on the carbonyl group: The rate of hydrate formation increases with a decrease in the number of alkyl groups attached to the carbonyl carbon. Hence,...

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Updated: Sep 25, 2025

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

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

Published on: November 9, 2019

Mining hydroformylation in complex reaction network via graph theory.

Keisuke Takahashi¹, Maeda Satoshi^1,2

¹Department of Chemistry, Hokkaido University North 10, West 8 Sapporo 060-8510 Japan keisuke.takahashi@sci.hokudai.ac.jp.

|April 28, 2022

Summary

Data science methods identified cobalt tetracarbonyl hydride as the key reactant in cobalt-catalyzed hydroformylation. The study revealed favored reaction paths, paving the way for deeper chemical reaction understanding.

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Area of Science:

Chemical Reaction Networks
Computational Chemistry
Data Science Applications

Background:

Understanding complex chemical reactions is crucial for catalysis.
Cobalt-catalyzed hydroformylation is an industrially relevant process.
Identifying reactants, products, and pathways is key to mechanistic elucidation.

Purpose of the Study:

To apply data science techniques for analyzing chemical reaction networks.
To identify the primary reactant, products, and reaction pathways in cobalt-catalyzed hydroformylation.
To determine the energetically favored reaction pathway.

Main Methods:

Utilizing first principles calculations to construct the reaction network.
Applying network analysis metrics like closeness centrality and betweenness centrality.
Analyzing energy profiles to determine reaction favorability.

Main Results:

Cobalt tetracarbonyl hydride was identified as the central reactant.
Three distinct reaction paths were uncovered, yielding aldehyde, CH2O, and CO2.
The pathway leading to aldehyde formation was determined to be energetically favored.

Conclusions:

Data science provides a powerful framework for dissecting complex chemical reaction networks.
The identified reactant and energetically favored pathway offer foundational insights into cobalt-catalyzed hydroformylation.
This approach serves as a crucial first step towards detailed kinetic studies.