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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.

Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis

Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis

Overview
Ethers can be prepared from organic compounds by various methods. Some of them are discussed below,
Preparation of Ethers by Alcohol Dehydration
In this method, in the presence of protic acids, alcohol dehydrates to produce alkenes and ethers under different conditions. For example, in the presence of sulphuric acid, dehydration of ethanol at 413 K yields ethoxyethane, whereas it yields ethene at 443 K.

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.

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.

Esters to Alcohols: Hydride Reductions

Esters to Alcohols: Hydride Reductions

Esters are reduced to primary alcohols when treated with a strong reducing agent like lithium aluminum hydride. The reaction requires two equivalents of the reducing agent and proceeds via an aldehyde intermediate.
Lithium aluminum hydride is a source of hydride ions and functions as a nucleophile. The mechanism proceeds in three steps. Firstly, the nucleophilic hydride ion attacks the carbonyl carbon of the ester to form a tetrahedral intermediate. Subsequently, the carbonyl group re-forms,...

Aldehydes and Ketones with Water: Hydrate Formation

Aldehydes and Ketones with Water: Hydrate Formation

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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Hierarchical and Programmable One-Pot Oligosaccharide Synthesis

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Reductive Hydroformylation of Isosorbide Diallyl Ether.

Jérémy Ternel¹, Adrien Lopes^1,2, Mathieu Sauthier²

¹University of Artois, CNRS, Centrale Lille, University of Lille, UMR 8181-UCCS-Unité de Catalyse et Chimie du Solide, F-62300 Lens, France.

Molecules (Basel, Switzerland)

|December 10, 2021

Summary

This study demonstrates a new method for creating valuable diols from isosorbide diallyl ether. Reductive hydroformylation achieved a high yield, showcasing a sustainable route to bio-sourced chemicals.

Keywords:

catalysis hydroformylation hydrogenation rhodium tandem reaction

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Area of Science:

Green chemistry and sustainable synthesis
Organic chemistry and catalysis
Biomass-derived chemicals

Background:

Isosorbide derivatives are key bio-sourced building blocks for various applications.
Efficient synthesis of functionalized isosorbide compounds is crucial for expanding their use.
Hydroxymethylation of carbon-carbon double bonds offers a pathway to valuable diols.

Purpose of the Study:

To investigate the reductive hydroformylation of isosorbide diallyl ether.
To synthesize bis-primary alcohols from a renewable resource.
To optimize a rhodium/amine catalytic system for this transformation.

Main Methods:

Utilized isosorbide diallyl ether as the substrate.
Employed a rhodium/amine catalytic system for reductive hydroformylation.
Performed hydroformylation followed by hydrogenation to convert double bonds to primary alcohols.

Main Results:

Achieved successful synthesis of bis-primary alcohols from isosorbide diallyl ether.
Obtained the highest yield of bis-primary alcohols at 79%.
Demonstrated the efficacy of the rhodium/amine catalyst system.

Conclusions:

Reductive hydroformylation is an effective method for synthesizing diols from isosorbide diallyl ether.
The developed catalytic system provides a high yield of desired bis-primary alcohols.
This research contributes to the sustainable production of bio-based chemicals.