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Related Concept Videos

Radical Anti-Markovnikov Addition to Alkenes: Overview01:25

Radical Anti-Markovnikov Addition to Alkenes: Overview

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The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.
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Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

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Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
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Crossed Aldol Reaction Using Strong Bases: Directed Aldol Reaction00:56

Crossed Aldol Reaction Using Strong Bases: Directed Aldol Reaction

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The reaction between two different carbonyl compounds comprising α hydrogen in the presence of a strong base like lithium diisopropylamide (LDA) to form a crossed aldol product is known as a directed aldol reaction. The directed aldol reaction is depicted in Figure 1.
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Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

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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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Radical Anti-Markovnikov Addition to Alkenes: Mechanism01:17

Radical Anti-Markovnikov Addition to Alkenes: Mechanism

4.0K
The reaction of hydrogen bromide with alkenes in the presence of hydroperoxides or peroxides proceeds via anti-Markovnikov addition. The radical chain reaction comprises initiation, propagation, and termination steps.
The mechanism starts with chain initiation, which involves two steps. In the first chain initiation step, a weak peroxide bond is homolytically cleaved upon mild heating to form two alkoxy radicals. In the second initiation step, a hydrogen atom is abstracted by the alkoxy...
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Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

Regioselectivity of Electrophilic Additions-Peroxide Effect

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In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
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Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
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Bridgehead Alkene-Enabled Strain-Driven Bioorthogonal Reaction.

Fayang Xie1, Haolin Jiang1,2, Xiangqian Jia1

  • 1School of Pharmaceutical Sciences, MOE Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology, Tsinghua University, Beijing 100084, China.

Organic Letters
|July 18, 2022
PubMed
Summary
This summary is machine-generated.

A new bioorthogonal reaction uses a strained bridgehead alkene (BHA) for inverse-electron-demand Diels-Alder (IEDDA) cycloadditions. This biocompatible method enables efficient in vitro protein labeling and pretargeted live cell imaging.

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Area of Science:

  • Organic Chemistry
  • Chemical Biology
  • Biotechnology

Background:

  • Bioorthogonal reactions are crucial for studying biological systems without interference.
  • Inverse-electron-demand Diels-Alder (IEDDA) reactions offer rapid and specific covalent bond formation.
  • Developing novel bioorthogonal chemistries with improved reactivity and biocompatibility is essential.

Purpose of the Study:

  • To report a novel bioorthogonal reaction based on bridgehead alkene (BHA)-enabled IEDDA cycloaddition.
  • To demonstrate the utility of a strained BHA derived from a natural product.
  • To apply this new reaction for in vitro protein labeling and pretargeted live cell imaging.

Main Methods:

  • Synthesis of a strained bridgehead alkene (BHA) from natural product β-caryophyllene.
  • Characterization of the BHA's reactivity in inverse-electron-demand Diels-Alder (IEDDA) cycloaddition reactions.
  • Application of the BHA-IEDDA reaction for labeling proteins in vitro and imaging in live cells.

Main Results:

  • A novel BHA was synthesized and shown to be highly reactive in IEDDA cycloadditions.
  • The BHA-enabled IEDDA reaction demonstrated excellent biocompatibility.
  • Successful in vitro protein labeling and pretargeted live cell imaging were achieved using the developed reaction.

Conclusions:

  • The BHA-enabled IEDDA reaction represents a powerful new tool in bioorthogonal chemistry.
  • This method offers a biocompatible and efficient approach for biological labeling and imaging.
  • The use of a readily accessible natural product derivative highlights potential for sustainable chemical biology tools.