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Elimination Reactions

Elimination Reactions

A nucleophile can react with an alkyl halide to give the substitution product by displacing the halogen. Or it can function as a base to give the elimination product by deprotonation of the neighboring carbon to form an alkene. In an elimination reaction, the substrate loses two groups from adjacent carbons forming at least one π bond. The carbon attached to the halogen is called the α carbon, while the adjacent carbon is called the β carbon; hence, these reactions are called...

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.

α-Alkylation of Ketones via Enolate Ions

α-Alkylation of Ketones via Enolate Ions

Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...

E2 Reaction: Stereochemistry and Regiochemistry

E2 Reaction: Stereochemistry and Regiochemistry

Elimination reactions of alkyl halides can yield one or more alkenes depending on the specific regiochemical and stereochemical considerations. While the regiochemistry of the reaction governs the location of the double bond in the product, the stereochemical requirements often influence the geometry.
When a substrate with two different β hydrogens undergoes an E2 elimination, the presence of a strong base can yield two regioisomeric alkenes. The more-substituted alkene is the major...

Preparation of Alkynes: Dehydrohalogenation

Preparation of Alkynes: Dehydrohalogenation

Introduction
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.

Nucleophilic Aromatic Substitution: Elimination–Addition

Nucleophilic Aromatic Substitution: Elimination–Addition

Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...

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Related Experiment Video

Updated: Jan 8, 2026

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

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Published on: September 12, 2018

Selective Reductive Elimination from Pd(IV)-Enabled Dual C-H Alkylation.

Qiongqiong Zhu¹, Xiang Zuo¹, Dongdong Tu¹

¹School of Chemical Science and Engineering, Tongji University, Shanghai 200092, China.

Organic Letters

|December 23, 2025

Summary

Researchers achieved selective reductive elimination from palladium(IV) complexes, a key step in organometallic chemistry. This breakthrough enables new dual C-H alkylation reactions for creating complex pyrrole products.

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Area of Science:

Organometallic Chemistry
Catalysis
Synthetic Organic Chemistry

Background:

Reductive elimination is a crucial step in many organometallic reactions.
Controlling selectivity in reductive elimination from palladium(IV) centers with two different aryl groups is challenging.

Purpose of the Study:

To investigate and achieve selective reductive elimination from C(aryl),C(pyrrolyl)-Pd(IV) complexes.
To develop novel dual C-H alkylation reactions based on this selective process.

Main Methods:

Synthesis of C(aryl),C(pyrrolyl)-Pd(IV) complexes.
Investigation of reductive elimination pathways under various conditions.
Development and optimization of dual C-H alkylation reaction conditions.

Main Results:

Selective reductive elimination was achieved at the pyrrolyl group of the Pd(IV) complexes.
The study successfully developed dual C-H alkylation reactions.
Dialkylated pyrrole products were synthesized with high efficiency.

Conclusions:

Selective reductive elimination from C(aryl),C(pyrrolyl)-Pd(IV) complexes is feasible.
This selectivity enables new synthetic routes for functionalized pyrroles.
The developed dual C-H alkylation offers a powerful tool for organic synthesis.