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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.

Hybridization of Atomic Orbitals I

Hybridization of Atomic Orbitals I

The mathematical expression known as the wave function, ψ, contains information about each orbital and the wavelike properties of electrons in an isolated atom. When atoms are bound together in a molecule, the wave functions combine to produce new mathematical descriptions that have different shapes. This process of combining the wave functions for atomic orbitals is called hybridization and is mathematically accomplished by the linear combination of atomic orbitals. The new orbitals that...

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:

Diazonium Group Substitution: –OH and –H

Diazonium Group Substitution: –OH and –H

Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.

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.

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Updated: Dec 17, 2025

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI

Published on: November 22, 2016

Isolable Diaminophosphide Boranes.

Markus Blum¹, Tobias Dunaj¹, Julius A Knöller¹

¹Institute of Inorganic Chemistry, University of Stuttgart, Pfaffenwaldring 55, 70550, Stuttgart, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|June 23, 2020

Summary

Alkali metal amides enable selective synthesis of metal diaminophosphide boranes. These compounds exhibit salt-like structures and show potential in creating novel phosphine boranes with unique functional groups.

Keywords:

alkali metals boranes nucleophiles phosphines phosphorus nitrogen compounds

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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI

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Area of Science:

Organometallic Chemistry
Borane Chemistry
Phosphorus Chemistry

Background:

Diaminophosphine boranes are versatile precursors in inorganic synthesis.
Developing efficient methods for metalation of these compounds is crucial for accessing new materials.

Purpose of the Study:

To establish a robust and selective synthetic route to metal diaminophosphide boranes.
To explore the structural characteristics and synthetic utility of these novel metalated species.

Main Methods:

Metalation of secondary diaminophosphine boranes using alkali metal amides.
In situ characterization by Nuclear Magnetic Resonance (NMR) spectroscopy.
Isolation and structural determination of metalated compounds using single-crystal X-ray diffraction (XRD).

Main Results:

A selective synthesis of metal diaminophosphide boranes (M[(R2N)2P(BH3)]) was achieved using alkali metal amides.
Characterization revealed salt-like structures with strong ionic interactions.
Synthetic applications demonstrated the formation of novel phosphine boranes with diverse functional groups.

Conclusions:

Metalation with alkali metal amides is a superior method compared to reduction for synthesizing metal diaminophosphide boranes.
The metalated species serve as valuable intermediates for constructing complex organophosphorus compounds.
Further studies may explore the removal of the borane fragment for expanded synthetic possibilities.