Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview01:19

α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview

3.3K
The pinacol and McMurry reactions involve the reductive coupling of ketones or aldehydes. Similarly, the bimolecular reductive coupling of two ester molecules in the presence of sodium metal in an aprotic solvent yields an α-hydroxy ketone product. The α-hydroxy ketone is also called acyloin, so the reaction is referred to as ‘acyloin condensation.’
3.3K
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

22.1K
Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
22.1K
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

3.2K
Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
3.2K
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

3.3K
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
3.3K
Preparation of Epoxides03:00

Preparation of Epoxides

10.0K
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 peroxy...
10.0K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

6.7K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
6.7K

You might also read

Related Articles

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

Sort by
Same author

USP16 regulates mitochondrial function by deubiquitinating TOM40, a core component of the translocase in the mitochondrial outer membrane.

Cell death & disease·2026
Same author

Correction: Xu et al. Mitochondria and Epigenetic Regulation: Bidirectional Crosstalk and Emerging Mitochondria-Targeted Degron Tools. <i>Cells</i> 2026, <i>15</i>, 95.

Cells·2026
Same author

Nickel-Catalyzed Cross-Dehydrogenative Allylation of Aldehydes.

Journal of the American Chemical Society·2026
Same author

Direct Acylation of Alkyl and Aryl Bromides via Nickel-Catalyzed Aldehyde C-H Functionalization.

The Journal of organic chemistry·2026
Same author

Integrated bioinformatics and machine learning approaches reveal that Venenum bufonis acts against acute pharyngitis by inhibiting the p38 MAPK/ERK-MKNK1-eIF4E signaling pathway.

Journal of ethnopharmacology·2026
Same author

Mitochondria and Epigenetic Regulation: Bidirectional Crosstalk and Emerging Mitochondria-Targeted Degron Tools.

Cells·2026

Related Experiment Video

Updated: Apr 16, 2026

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
09:58

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

Published on: February 24, 2015

11.8K

Exo-selective reductive macrocyclization of ynals.

Hengbin Wang1, Solymar Negretti1, Allison R Knauff1

  • 1Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109-1055, United States.

Organic Letters
|March 10, 2015
PubMed
Summary

A new nickel-catalyzed method enables the highly selective synthesis of large ring compounds called macrocycles. This protocol efficiently produces exoalkylidene macrocycles from simple starting materials.

More Related Videos

Solid-phase Synthesis of [4.4] Spirocyclic Oximes
05:15

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

7.4K
A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

8.8K

Related Experiment Videos

Last Updated: Apr 16, 2026

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
09:58

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

Published on: February 24, 2015

11.8K
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
05:15

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

7.4K
A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

8.8K

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Chemistry

Background:

  • Macrocycles are important in various fields, including medicine and materials science.
  • Selective synthesis of macrocycles, particularly with specific substituents, remains a challenge.
  • Existing methods often favor endo-selective products, limiting access to exo-isomers.

Purpose of the Study:

  • To develop a general protocol for the highly exo-selective macrocyclization of ynals.
  • To synthesize 10- to 21-membered macrocycles with an exomethylene substituent.
  • To achieve high yields, regioselectivity, and diastereocontrol in macrocycle synthesis.

Main Methods:

  • Utilized a nickel/N-heterocyclic carbene catalyst system.
  • Employed ynals as starting materials for macrocyclization.
  • Investigated the scope and limitations of the developed protocol.

Main Results:

  • Achieved highly exo-selective macrocyclization of ynals (>95:5 exo/endo ratio).
  • Synthesized a series of 10- to 21-membered macrocycles in good yields.
  • Demonstrated high levels of long-range diastereocontrol for certain macrocycle classes.
  • Provided access to exoalkylidene macrocycles, complementary to endo-selective methods.

Conclusions:

  • The developed nickel-catalyzed protocol offers a powerful and selective route to exoalkylidene macrocycles.
  • This method expands the synthetic toolbox for accessing diverse macrocyclic structures.
  • The protocol's high selectivity and control offer significant advantages for future macrocycle synthesis.