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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.

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.

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.

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...

Alcohols from Carbonyl Compounds: Reduction

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Reduction is a simple strategy to convert a carbonyl group to a hydroxyl group. The three major pathways to reduce carbonyls to alcohols are catalytic hydrogenation, hydride reduction, and borane reduction.
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...

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.

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Updated: Aug 1, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

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Aldehyde Olefination with Arylboroxines Enabled by Binary Rhodium Catalysis.

Zihao Zhang^1,2, Jie Jia², Fangdong Hu¹

¹School of Chemistry and Chemical Engineering, Linyi University, Linyi 276000, China.

Organic Letters

|April 27, 2023

Summary

This study introduces a rhodium-catalyzed olefination reaction using simple rhodium complexes. The method efficiently produces aryl olefins from aliphatic aldehydes and arylboroxines under mild conditions.

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Area of Science:

Organic Chemistry
Organometallic Chemistry
Catalysis

Background:

Olefination reactions are crucial for synthesizing carbon-carbon double bonds.
Developing efficient and mild catalytic systems for olefination remains an active research area.

Purpose of the Study:

To describe a novel rhodium-catalyzed olefination of aliphatic aldehydes with arylboroxines.
To achieve efficient synthesis of aryl olefins with broad functional group tolerance.

Main Methods:

Utilized a simple rhodium(I) complex, [Rh(cod)OH]2, as a catalyst.
Conducted the reaction under air and neutral conditions without external ligands or additives.
Performed mechanistic investigations to elucidate the catalytic pathway.

Main Results:

Successfully synthesized aryl olefins from aliphatic aldehydes and arylboroxines.
Demonstrated high efficiency and good functional group tolerance.
Identified a binary rhodium catalysis mechanism involving Rh(I)-catalyzed 1,2-addition and Rh(III)-catalyzed elimination.

Conclusions:

The developed rhodium-catalyzed olefination offers an efficient route to aryl olefins.
The catalytic system operates under mild, air-stable, and neutral conditions.
The mechanistic insights provide a foundation for further catalyst development.