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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

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.
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α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction

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The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the...
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Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

10.7K
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.
10.7K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

9.2K
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.
9.2K
Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism01:14

Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism

4.7K
The Wittig reaction, which converts aldehydes or ketones to alkenes using phosphorus ylides, proceeds through a nucleophilic addition‒elimination process.
The reaction begins with the nucleophilic addition between a phosphorus ylide and the carbonyl compound. Due to its carbanionic character,  phosphorus ylide acts as a strong nucleophile and attacks the electrophilic carbonyl group. This generates a charge-separated dipolar intermediate called betaine. The negatively charged oxygen atom and...
4.7K
Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

6.3K
In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
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Updated: Dec 17, 2025

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

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Easy Access to Phosphine-Borane Building Blocks.

G Bas de Jong1,2, Nuria Ortega2, Martin Lutz3

  • 1Van't Hoff Institute for Molecular Sciences (HIMS), University of Amsterdam, P.O. Box 94157, 1090 GD, Amsterdam, The Netherlands.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|July 1, 2020
PubMed
Summary
This summary is machine-generated.

Researchers developed a new method for synthesizing primary phosphine-boranes using lithium borohydride. This approach provides stable building blocks for various applications, including organophosphorus chemistry.

Keywords:
crystal structuresphosphanediidephosphine boraneprimary phosphinesynthesis

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Area of Science:

  • Organometallic Chemistry
  • Inorganic Chemistry
  • Synthetic Chemistry

Background:

  • Primary phosphines are valuable synthetic intermediates.
  • Handling and storage of primary phosphines can be challenging due to their reactivity and instability.
  • Borane protection offers a strategy to stabilize reactive phosphine species.

Purpose of the Study:

  • To develop a facile and efficient method for the synthesis of primary phosphine-boranes.
  • To provide stable and handleable precursors for organophosphorus compounds.
  • To explore the deprotonation of phosphine-boranes to generate phosphanediides.

Main Methods:

  • Synthesis of primary phosphine-boranes (RPH2·BH3) from dichlorophosphines using Li[BH4].
  • Utilizing Li[BH4] as both a reductant and a source of the BH3 protecting group.
  • Double deprotonation of borane-protected primary phosphines with n-butyllithium.

Main Results:

  • Facile access to a variety of alkyl-, aryl-, and aminophosphine-boranes.
  • Aminophosphine-boranes are obtained as stable compounds, overcoming handling difficulties associated with unprotected aminophosphines.
  • Formation of soluble phosphanediides (Li2[RP·BH3]) through double deprotonation.
  • Structural characterization of the phenyl-derivative, Li2[PhP·BH3].

Conclusions:

  • The developed method provides a straightforward route to stable primary phosphine-boranes.
  • Borane protection enhances the stability and handleability of primary phosphines, including aminophosphine derivatives.
  • The phosphanediides are versatile intermediates in organophosphorus synthesis.