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Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

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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.
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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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Regioselectivity and Stereochemistry of Hydroboration02:36

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.
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Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

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Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.
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Amines to Alkenes: Cope Elimination01:14

Amines to Alkenes: Cope Elimination

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Cope elimination reaction involves the conversion of tertiary amines to alkene using hydrogen peroxide under thermal conditions, as depicted in figure 1.
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Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation01:28

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

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Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...
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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

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Magnesocenophane-Catalyzed Amine Borane Dehydrocoupling.

Lisa Wirtz1, Wasim Haider1, Volker Huch1

  • 1Faculty of Natural Science and Technology, Department of Chemistry, Saarland University, Campus Saarbrücken, 66123, Saarbrücken, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|February 14, 2020
PubMed
Summary
This summary is machine-generated.

Magnesocenophanes exhibit Lewis acidity influenced by cyclopentadienyl tilt. C[1]magnesocenophane effectively catalyzes amine borane dehydrogenation under ambient conditions via a ligand-assisted mechanism.

Keywords:
amine boranescatalysisdehydrocouplingmagnesiummetallocenophanes

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Computational Chemistry

Background:

  • [n]Magnesocenophanes are organometallic compounds with potential catalytic applications.
  • Lewis acidity is a key property influencing catalytic activity.
  • Amine borane dehydrogenation is an important reaction for hydrogen storage and synthesis.

Purpose of the Study:

  • To investigate the Lewis acidities of [n]magnesocenophanes.
  • To explore their catalytic activity in amine borane dehydrogenation/dehydrocoupling.
  • To elucidate the reaction mechanism.

Main Methods:

  • Computational investigation of Lewis acidities.
  • Experimental and computational studies of catalytic reactions.
  • Analysis of reaction intermediates and mechanisms.

Main Results:

  • Lewis acidity of [n]magnesocenophanes correlates with cyclopentadienyl moiety tilt.
  • C[1]magnesocenophane efficiently catalyzes dimethylamine borane and diisopropylamine borane dehydrogenation/dehydrocoupling at ambient conditions.
  • A ligand-assisted mechanism involving stepwise proton and hydride transfer was proposed for dimethylamine borane dehydrogenation.

Conclusions:

  • The structure of [n]magnesocenophanes significantly impacts their Lewis acidity.
  • C[1]magnesocenophane is a promising catalyst for amine borane transformations.
  • Understanding the reaction mechanism provides insights for catalyst design and optimization.