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Related Concept Videos

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
Preparation of Alcohols via Addition Reactions02:15

Preparation of Alcohols via Addition Reactions

Overview
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...
Hydroboration-Oxidation of Alkenes03:08

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.
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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.
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.

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Reenvisioning the De Mayo Reaction: A Boron-Enabled Cycloaddition Approach.

Neetu Sharma1, Yanyao Liu1, Partha Sarathi Hazra1

  • 1Department of Chemistry, Indiana University, Bloomington, Indiana, USA.

Angewandte Chemie (International Ed. in English)
|June 3, 2026
PubMed
Summary

This study revises the De Mayo reaction using alkenylboronates for controlled synthesis of 1,5-dicarbonyls. A novel oxy-boracycle intermediate enables bimolecular cycloaddition, expanding synthetic utility.

Keywords:
De Mayoconformational lockcycloadditionenergy transferphotochemistry

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • The De Mayo reaction is a classic method for synthesizing 1,5-dicarbonyls and cyclobutanols.
  • Traditional methods have limitations in control and scope.

Purpose of the Study:

  • To develop a revised De Mayo reaction utilizing alkenylboronates.
  • To achieve delayed and controlled synthesis of De Mayo products.
  • To explore the reactivity of the C-B bond in the products.

Main Methods:

  • Utilized alkenylboronates as surrogates for 1,3-dicarbonyls.
  • Investigated a novel reaction pathway involving a rigid oxy-boracycle intermediate.
  • Performed mechanistic experiments to elucidate the reaction pathway.

Main Results:

  • Successfully synthesized 1,5-dicarbonyls with enhanced control.
  • Demonstrated the formation and utility of a rigid oxy-boracycle intermediate.
  • Showcased the elaboration of the C-B bond in the resulting products.

Conclusions:

  • The revised De Mayo reaction offers a controlled and versatile approach to 1,5-dicarbonyl synthesis.
  • The identification of the oxy-boracycle intermediate is crucial for the bimolecular cycloaddition.
  • This work expands the synthetic applications of alkenylboronates in cycloaddition reactions.