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Related Concept Videos

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

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.
Regioselectivity and Stereochemistry of Hydroboration02:36

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.
Hydroboration-Oxidation of Alkenes03:08

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.
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
Preparation of Alcohols via Addition Reactions02:15

Preparation of Alcohols via Addition Reactions

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...
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...

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

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Boron azides in Staudinger oxidations and cycloadditions.

Rebecca L Melen1, Alan J Lough, Douglas W Stephan

  • 1Department of Chemistry and University of Toronto, 80 St. George Street, Toronto, Ontario, Canada M5S 3H6.

Dalton Transactions (Cambridge, England : 2003)
|May 9, 2013
PubMed
Summary

The Staudinger reaction between boron-nitrogen compounds and phosphines creates novel boron-nitrogen-phosphorus systems. These reactions can lead to unique bicyclic and dimeric products depending on reaction conditions and phosphine type.

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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
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Published on: February 7, 2019

Area of Science:

  • Organometallic Chemistry
  • Synthetic Chemistry
  • Materials Science

Background:

  • The Staudinger reaction is a well-established method for forming P-N bonds.
  • Boron-nitrogen compounds offer unique electronic and structural properties.
  • Exploring new synthetic routes to organoboron and organophosphorus compounds is crucial for materials development.

Purpose of the Study:

  • To investigate the Staudinger reaction of boron azides with various tri-substituted phosphines.
  • To synthesize and characterize novel boron-nitrogen-phosphorus linked systems.
  • To explore the influence of phosphine structure and reaction conditions on product formation.

Main Methods:

  • Staudinger reaction utilizing boron azides (Cy2BN3 and (C6F5)2BN3) and tri-substituted phosphines.
  • X-ray diffraction for structural elucidation of synthesized compounds.
  • Varying phosphine substituents and reaction conditions to control product outcome.

Main Results:

  • Synthesis of boron-nitrogen-phosphorus linked systems (1a-d and 2a-d) through Staudinger reactions.
  • Formation of a bicyclic product (3) via a dual Staudinger and cycloaddition pathway.
  • Generation of an unusual dimeric product (4) when the Staudinger reaction was inhibited by phosphine oxidation.
  • Structural confirmation of key products (1b-d, 2b-d, 3, and 4) via X-ray diffraction.

Conclusions:

  • The Staudinger reaction provides a versatile route to diverse boron-nitrogen-phosphorus compounds.
  • Reaction pathways can be tuned to yield linear, bicyclic, or dimeric structures.
  • Understanding these reaction mechanisms is key to designing novel organoboron and organophosphorus materials.