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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 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.

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.

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.

Radical Anti-Markovnikov Addition to Alkenes: Overview

Radical Anti-Markovnikov Addition to Alkenes: Overview

The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.

Radical Anti-Markovnikov Addition to Alkenes: Mechanism

Radical Anti-Markovnikov Addition to Alkenes: Mechanism

The reaction of hydrogen bromide with alkenes in the presence of hydroperoxides or peroxides proceeds via anti-Markovnikov addition. The radical chain reaction comprises initiation, propagation, and termination steps.
The mechanism starts with chain initiation, which involves two steps. In the first chain initiation step, a weak peroxide bond is homolytically cleaved upon mild heating to form two alkoxy radicals. In the second initiation step, a hydrogen atom is abstracted by the alkoxy...

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Selective Hydroboration-Oxidation of Terminal Alkenes under Flow Conditions.

Mohamed Elsherbini¹, Florence Huynh¹, Alice Dunbabin¹

¹School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, CF10 3AT, UK.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|April 25, 2020

Summary

A new flow process efficiently converts amorpha-4,11-diene to an artemisinin precursor alcohol using 9-borabicyclo(3.3.1)nonane (9-BBN). This cost-effective method utilizes in situ generated 9-BBN for high-productivity synthesis.

Keywords:

alcohols alkenes flow chemistry hydroboration oxidation

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Area of Science:

Organic Chemistry
Process Chemistry
Medicinal Chemistry

Background:

Artemisinin is a crucial antimalarial drug.
Efficient synthesis of artemisinin intermediates is vital.
Hydroboration-oxidation is a key transformation for alcohol synthesis.

Purpose of the Study:

To develop an efficient flow process for alkene hydroboration-oxidation.
To synthesize a key intermediate for artemisinin using 9-borabicyclo(3.3.1)nonane (9-BBN).
To establish a cost-effective method for in situ 9-BBN generation.

Main Methods:

Utilized a flow reactor for selective hydroboration and oxidation of alkenes.
Employed 9-borabicyclo(3.3.1)nonane (9-BBN) as the boron source.
Generated 9-BBN in situ via the reaction of borane and 1,5-cyclooctadiene in a flow generator.

Main Results:

Achieved facile conversion of amorpha-4,11-diene to the corresponding alcohol.
Demonstrated high productivity of 1.4 g/h for the transformation.
Showcased the cost-efficiency of in situ 9-BBN generation.

Conclusions:

The developed flow process enables efficient and selective synthesis of artemisinin intermediates.
In situ generation of 9-BBN in a flow system offers a practical and economical approach.
This method facilitates the production of advanced intermediates for antimalarial drug synthesis.