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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.

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 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.

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Dipole Moment of a Molecule

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...

Exceptions to the Octet Rule

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Many covalent molecules have central atoms that do not have eight electrons in their Lewis structures. These molecules fall into three categories:

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Related Experiment Video

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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

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Mono- and di-cationic hydrido boron compounds.

Rajendra S Ghadwal¹, Christian J Schürmann, Diego M Andrada

¹Institut für Anorganische Chemie, Universität Bielefeld, Universitätsstrasse 25, 33615 Bielefeld, Germany. rghadwal@uni-bielefeld.de.

Dalton Transactions (Cambridge, England : 2003)

|July 23, 2015

Summary

This study details the synthesis of novel cationic boron compounds via Brønsted acid-mediated hydride abstraction. These unique compounds exhibit interesting electronic and structural properties, featuring three-center two-electron bonds.

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Area of Science:

Organometallic Chemistry
Boron Chemistry
Catalysis

Background:

Boron hydrides are versatile precursors in synthetic chemistry.
Cationic boron compounds offer unique reactivity and structural motifs.
Understanding hydride abstraction is key to developing new boron-based materials.

Purpose of the Study:

To synthesize and characterize novel cationic hydrido boron compounds.
To investigate the electronic and structural properties of these unique species.
To explore the utility of Brønsted acid-mediated dehydrogenative hydride abstraction.

Main Methods:

Dehydrogenative hydride abstraction using Brønsted acid HNTf2.
Synthesis of mono-cationic and di-cationic hydrido boron compounds.
Characterization using spectroscopic (NMR, IR), crystallographic, and computational methods.

Main Results:

Formation of thermally stable mono-cationic [{(L)BH2}2(μ-H)](NTf2) and di-cationic [{(L)BH}2(μ-H)2](NTf2)2 compounds.
Isolation of unique cationic boron compounds featuring CH2BH2(μ-H)BH2CH2 and CH2BH(μ-H)2BHCH2 moieties.
Confirmation of three-center two-electron (3c-2e) bonding within these cationic structures.

Conclusions:

The study successfully synthesized and characterized novel cationic hydrido boron compounds.
These compounds exhibit unique structural features and 3c-2e bonding.
The findings contribute to the understanding of boron chemistry and hydride abstraction reactions.