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Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

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If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
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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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Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

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Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene01:17

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The electrophilic addition of hydrogen halides such as HBr to alkenes and nonconjugated dienes gives a single product as per Markovnikov’s rule.
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The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
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Arene diversification through distal C(sp2)-H functionalization.

Uttam Dutta1, Sudip Maiti1, Trisha Bhattacharya1

  • 1Indian Institute of Technology Bombay, Powai, Mumbai 400076, India.

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|May 14, 2021
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Summary
This summary is machine-generated.

This review covers advances in transition metal-catalyzed distal C-H activation. It highlights strategies for site-selective functionalization, overcoming challenges in meta- and para-C-H bond activation.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Transition metal-catalyzed C-H activation offers efficient synthesis routes.
  • Distal C-H activation (meta/para) is challenging due to steric and electronic factors.
  • Site-selective functionalization is key for complex molecule synthesis.

Purpose of the Study:

  • To review recent strategies for controlling distal aryl C-H activation.
  • To highlight methods overcoming challenges in meta- and para-functionalization.
  • To showcase advancements in catalyst and ligand design for C-H activation.

Main Methods:

  • Review of literature on directing group strategies.
  • Analysis of transient mediators and traceless directors.
  • Examination of noncovalent interactions in catalysis.
  • Evaluation of catalyst and ligand effects on selectivity.

Main Results:

  • Demonstration of successful directing group assistance for distal C-H activation.
  • Exploration of novel transient and traceless directing strategies.
  • Understanding the role of noncovalent interactions in regioselectivity.
  • Identification of key catalyst and ligand features for distal activation.

Conclusions:

  • Distal C-H activation is achievable through sophisticated catalyst and template design.
  • Multiple strategies exist to overcome inherent challenges in meta- and para-functionalization.
  • This review provides insights into advancing site-selective C-H functionalization.