Search research articles

ABOUT JoVE

Overview Leadership Blog JoVE Help Center

AUTHORS

Publishing Process Editorial Board Scope & Policies Peer Review FAQ Submit

LIBRARIANS

Testimonials Subscriptions Access Resources Library Advisory Board FAQ

RESEARCH

JoVE Journal Methods Collections JoVE Encyclopedia of Experiments Archive

EDUCATION

JoVE Core JoVE Business JoVE Science Education JoVE Lab Manual Faculty Resource Center Faculty Site

Terms & Conditions of Use

Related Concept Videos

Hydroboration-Oxidation of Alkenes

Hydroboration-Oxidation of Alkenes

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.

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.

Regioselectivity and Stereochemistry of Hydroboration

Regioselectivity and Stereochemistry of Hydroboration

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...

Preparation of Epoxides

Preparation of Epoxides

Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of...

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

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

The electrophilic addition of hydrogen halides such as HBr to alkenes and nonconjugated dienes gives a single product as per Markovnikov’s rule.

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

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

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

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by

Same author

Catalyst-controlled site-selective dehydrogenation, a stepping stone for C-H oxidations in complex terpenes synthesis.

Nature communications·2026

Same author

A novel AIE + ESIPT mechanism-based fluorescent probe for selective detection and imaging of cysteine in living cells.

Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy·2026

Same author

Conformation-driven C3-C(<i>sp</i> <sup>3</sup>)-H arylation of saturated azacycles using Pd catalyst.

Nature catalysis·2026

Same author

Polarization-State-Dependent Charge Screening in Metal-Ferroelectric-Metal Memcapacitors Enabled by an IGZO Oxygen Reservoir Layer.

ACS applied materials & interfaces·2026

Same author

A NAMs-based framework for screening the endocrine-disrupting potential of plastic additives using cross-species molecular docking and <i>Caenorhabditis elegans</i>.

Frontiers in toxicology·2026

Same author

Ligand-Enabled Stereoselective Coupling of Methylene C(sp<sup>3</sup>)─H Bonds With Alkenyl Bromide via Pd<sup>II</sup>/Pd<sup>0</sup>/Pd<sup>II</sup> Catalysis.

Angewandte Chemie (International ed. in English)·2026

Search research articles

Related Experiment Video

Updated: Sep 17, 2025

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

Versatile Butenolide Syntheses via a Structure-Oriented C-H Activation Reaction.

Yu-Kun Lin¹, Donghyeon Kim¹, Yuxin Ouyang¹

¹Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.

Journal of the American Chemical Society

|July 3, 2025

Summary

This study introduces a novel palladium catalyst for the one-step synthesis of butenolides from aliphatic acids. This C-H activation method efficiently creates complex molecules using readily available starting materials.

More Related Videos

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Published on: May 26, 2019

Related Experiment Videos

Last Updated: Sep 17, 2025

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Published on: May 26, 2019

Area of Science:

Organic Chemistry
Catalysis
Medicinal Chemistry

Background:

C-H activation has advanced, but one-step synthesis of complex scaffolds from simple feedstocks remains challenging.
Butenolides are crucial pharmacophores and synthetic intermediates, driving demand for efficient synthesis methods.

Purpose of the Study:

To develop a novel catalytic system for the one-step synthesis of butenolides via structure-oriented C-H activation.
To enable the efficient functionalization of abundant aliphatic acids into valuable butenolide structures.

Main Methods:

Development of a palladium catalyst featuring a unique triazole-pyridone ligand.
Utilizing tert-butyl hydroperoxide (TBHP) as the sole oxidant for triple C(sp3)-H bond functionalization.
Employing diverse aliphatic acids as feedstock chemicals.

Main Results:

Achieved a one-step conversion of aliphatic acids to butenolides through triple C-H bond functionalization.
Demonstrated the catalyst's effectiveness with low catalyst loading (1 mol %) and scalability.
Facilitated improved syntheses of bioactive natural products and drug candidates, including anticancer and anti-HIV compounds.

Conclusions:

The developed palladium catalyst and ligand system enable a highly efficient and practical butenolide synthesis.
This method provides rapid access to novel and medicinally relevant butenolide chemical space.
The reaction's scalability and simple purification offer significant advantages for C-H activation applications.