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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

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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.

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...

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

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Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation...

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

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The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.

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The transition metal-catalysed hydroboration reaction.

Stephen J Geier¹, Christopher M Vogels¹, Jennifer A Melanson¹

¹Department of Chemistry and Biochemistry, Mount Allison University, Sackville, NB E4L 1G8, Canada. sgeier@mta.ca.

Chemical Society Reviews

|October 7, 2022

Summary

Transition metal catalysis enables hydridoborane addition to unsaturated molecules. This reaction now utilizes earth-abundant catalysts and diverse substrates, serving as a key tool in modern synthetic chemistry.

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Area of Science:

Organometallic Chemistry
Catalysis
Organic Synthesis

Background:

The addition of hydridoboranes to unsaturated organic molecules, catalyzed by transition metals, has a long history.
Interest in this reaction declined after initial discovery but has recently resurged.
Modern applications leverage earth-abundant metal catalysts and a broader scope of organic substrates.

Purpose of the Study:

To review recent advances in transition metal-catalyzed hydridoborane addition reactions.
To highlight the utility of this reaction in assessing new catalytic complexes.
To provide an overview of developments up to early 2022.

Main Methods:

Literature review of catalytic hydridoborane addition reactions.
Focus on transition metal and main group complexes.
Exclusion of reactions involving diboron sources.

Main Results:

Significant expansion in the range of applicable catalysts, including earth-abundant metals.
Broadened substrate scope for unsaturated organic molecules.
Established use as a diagnostic tool for catalyst evaluation.

Conclusions:

Transition metal-catalyzed hydridoborane addition is a rapidly advancing field.
The reaction's versatility makes it invaluable for catalyst discovery and organic synthesis.
Continued research promises further innovations in catalytic efficiency and substrate scope.