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Related Concept Videos

Conjugate Addition to α,β-Unsaturated Carbonyl Compounds01:09

Conjugate Addition to α,β-Unsaturated Carbonyl Compounds

α,β-Unsaturated carbonyl compounds are molecules bearing a carbonyl and alkene functionality in conjugation with each other. The conjugation in the molecule leads to three resonance structures. The hybrid form exhibits two probable electrophilic sites: the carbonyl carbon and the β carbon.
Carbocations02:10

Carbocations

Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...
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.
Conjugate Addition (1,4-Addition) vs Direct Addition (1,2-Addition)01:27

Conjugate Addition (1,4-Addition) vs Direct Addition (1,2-Addition)

α,β-Unsaturated carbonyl compounds with two electrophilic sites, the carbonyl carbon, and the β carbon, are susceptible to nucleophilic attack via two modes: conjugate or 1,4-addition and direct or 1,2-addition.
Conjugate addition results in a thermodynamically stable product. The reaction retains the stronger C=O bond at the expense of the weaker C=C π bond. The process is slow as the β carbon is less electrophilic than the carbonyl carbon.
Direct addition products are formed faster owing to...
Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene01:17

Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene

The electrophilic addition of hydrogen halides such as HBr to alkenes and nonconjugated dienes gives a single product as per Markovnikov’s rule.
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.

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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
07:36

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

1,1-Carboboration.

Gerald Kehr1, Gerhard Erker

  • 1Organisch-Chemisches Institut der Universität Münster, Corrensstr. 40, 48149 Münster, Germany. kehrald@uni-muenster.de

Chemical Communications (Cambridge, England)
|November 26, 2011
PubMed
Summary
This summary is machine-generated.

Highly electrophilic boranes enable efficient 1,1-carboboration reactions with various alkynes. This expands synthetic routes to valuable alkenylboranes and functionalized metallacycles.

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Area of Science:

  • Organoboron chemistry
  • Synthetic organic chemistry

Background:

  • The 1,1-carboboration reaction is a key transformation in organic synthesis.
  • Expanding the substrate scope and efficiency of carboboration is of significant interest.

Purpose of the Study:

  • To investigate the utility of highly electrophilic boranes, specifically RB(C6F5)2, in carboboration reactions.
  • To explore the application of these reagents with a diverse range of alkynyl substrates.

Main Methods:

  • Reaction of RB(C6F5)2 with terminal and internal alkynes.
  • Investigation of reactions with phosphorus-substituted alkynes and bisalkynyl substrates.
  • Characterization of the resulting alkenylborane and metallacyclic products.

Main Results:

  • RB(C6F5)2 reagents efficiently promote 1,1-carboboration of terminal alkynes under mild conditions, yielding valuable alkenylboranes.
  • Internal alkynes undergo 1,1-carboboration, offering a novel method for carbon-carbon sigma-bond activation.
  • Functionalized metallacyclic products are formed from complex substrates via selective carboboration sequences.

Conclusions:

  • Highly electrophilic boranes RB(C6F5)2 significantly broaden the scope of 1,1-carboboration.
  • These reactions provide efficient and versatile routes to synthetically useful organoboron compounds and metallacycles.