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Related Concept Videos

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
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

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Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
3.3K
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

7.3K
The electrophilic addition of hydrogen halides such as HBr to alkenes and nonconjugated dienes gives a single product as per Markovnikov’s rule.
7.3K
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
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

20.4K
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.
20.4K
Halogenation of Alkenes02:46

Halogenation of Alkenes

18.2K
Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
18.2K

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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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Intramolecular (directed) electrophilic C-H borylation.

S A Iqbal1, J Pahl1, K Yuan1

  • 1EastCHEM School of Chemistry, University of Edinburgh, Edinburgh, EH9 3FJ, UK. mingleso@ed.ac.uk.

Chemical Society Reviews
|June 5, 2020
PubMed
Summary
This summary is machine-generated.

This study explores transition metal-free intramolecular C-H borylation, a powerful method for creating carbon-boron bonds. It details mechanisms and highlights applications in materials science, organo-boronate esters, and bioactive compounds.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Materials Science

Background:

  • Intramolecular C-H borylation offers a metal-free route to carbon-boron bonds.
  • Existing methods primarily involve electrophilic boranes and focus on C-B and N-B bond formation.

Purpose of the Study:

  • To summarize and analyze intramolecular electrophilic C-H borylation reactions.
  • To elucidate the mechanisms and scope of these borylation reactions.
  • To highlight applications in organic materials, organo-boronate esters, and bioactive compounds.

Main Methods:

  • Review and mechanistic analysis of published intramolecular C-H borylation studies.
  • Discussion of reactions involving electrophilic boranes and various heteroatom bond formations (N-B, O-B, S-B, P-B).

Main Results:

  • Two primary mechanisms identified: electrophilic aromatic substitution and σ-bond metathesis.
  • Demonstration of applicability beyond conjugated materials to versatile organo-boronate esters and bioactives.
  • Identification of key requirements, regioselectivity factors, and substrate scope limitations.

Conclusions:

  • Intramolecular C-H borylation is a versatile and powerful transition metal-free synthetic strategy.
  • Understanding reaction mechanisms and key factors is crucial for optimizing synthetic procedures.
  • The methodology holds significant potential for diverse applications in chemistry and materials science.