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Halogenation of Alkenes02:46

Halogenation of Alkenes

15.2K
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.
15.2K
α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction

2.9K
The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the...
2.9K
Introduction to Electrophilic Addition Reactions of Alkenes02:24

Introduction to Electrophilic Addition Reactions of Alkenes

7.7K
The double bond in a simple, unconjugated alkene is a region of high electron density that can act as a weak base or a nucleophile. The filled π orbital (HOMO) of the double bond can interact with the empty LUMO of an electrophile. A bonding interaction occurs when the electrophile attacks between the two carbons; the electrophile then accepts a pair of electrons from the π bond and undergoes addition across the double bond, yielding a single product.
Addition and elimination...
7.7K
Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism01:14

Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism

3.3K
The Wittig reaction, which converts aldehydes or ketones to alkenes using phosphorus ylides, proceeds through a nucleophilic addition‒elimination process.
The reaction begins with the nucleophilic addition between a phosphorus ylide and the carbonyl compound. Due to its carbanionic character,  phosphorus ylide acts as a strong nucleophile and attacks the electrophilic carbonyl group. This generates a charge-separated dipolar intermediate called betaine. The negatively charged oxygen atom and...
3.3K
Reactions at the Benzylic Position: Halogenation01:11

Reactions at the Benzylic Position: Halogenation

2.3K
Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
2.3K
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

2.3K
Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
2.3K

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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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Halogen bond-catalyzed Pictet-Spengler reaction.

Mattis Damrath1, Alessandra Döring1, Boris J Nachtsheim1

  • 1Institute for Organic and Analytical Chemistry, University of Bremen, 28359 Bremen, Germany. nachtsheim@uni-bremen.de.

Chemical Communications (Cambridge, England)
|March 4, 2025
PubMed
Summary

This study introduces a metal-free halogen bond-catalyzed Pictet-Spengler reaction using diaryliodonium salts. This efficient method synthesizes tetrahydro-β-carbolines (THβCs) from tryptamines and carbonyl compounds with high yields.

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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Medicinal Chemistry

Background:

  • Traditional acid catalysis for the Pictet-Spengler reaction can be harsh.
  • Metal catalysts often pose environmental and cost concerns.
  • Developing metal-free catalytic systems is a key goal in synthetic chemistry.

Purpose of the Study:

  • To develop an efficient, metal-free catalytic system for the Pictet-Spengler reaction.
  • To utilize halogen bonding as a catalytic activation mode.
  • To broaden the substrate scope and applicability of the Pictet-Spengler reaction.

Main Methods:

  • Employing diaryliodonium salts as halogen bond catalysts.
  • Systematic optimization of catalyst loading and reaction conditions.
  • Utilizing various N-protected tryptamines and carbonyl compounds as substrates.

Main Results:

  • Achieved exceptional catalytic activity with 0.5 mol% dibenzoiodolium catalyst.
  • Synthesized tetrahydro-β-carbolines (THβCs) in up to 98% yield.
  • Demonstrated broad substrate scope including aromatic, heteroaromatic, and aliphatic aldehydes.
  • Successfully performed an oxa-Pictet-Spengler variant using tryptophol.

Conclusions:

  • Halogen bond catalysis offers an efficient, metal-free alternative for Pictet-Spengler reactions.
  • The developed protocol is versatile and high-yielding.
  • Control experiments confirmed the essential role of halogen bonding in catalysis.