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Related Concept Videos

Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

3.8K
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.
3.8K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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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.
2.9K
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

2.4K
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).
2.4K
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

6.5K
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
6.5K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.2K
Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
2.2K
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)

2.8K
Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
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Remote ortho-C-H functionalization via medium-sized cyclopalladation.

Mario Martínez Mingo1, Nuria Rodríguez1,2, Ramón Gómez Arrayás1,2

  • 1Department of Organic Chemistry, Universidad Autónoma de Madrid (UAM), Facultad de Ciencias, Cantoblanco, 28049, Madrid, Spain. n.rodriguez@uam.es.

Chemical Communications (Cambridge, England)
|January 27, 2022
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Summary

This review covers new methods for remote C-H functionalization using larger metalacycles. These strategies offer novel synthetic routes for creating complex molecules.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Chemistry

Background:

  • Directed ortho-C-H functionalization via five- or six-membered cyclopalladation is well-established.
  • Activating more remote C-H bonds using larger metalacycles (seven- or eight-membered) is significantly more challenging and less common.

Purpose of the Study:

  • To provide an overview of recent strategies for remote C-H functionalization.
  • To highlight the mechanistic details, synthetic utility, and limitations of these emerging methods.

Main Methods:

  • Focuses on strategies employing mono-anionic bidentate or monodentate directing groups.
  • Reviews recent research advancements in the field of remote C-H activation.

Main Results:

  • Demonstrates the increasing viability of larger metalacycle-mediated C-H functionalization.
  • Highlights the potential for selective C-C and C-X bond formation at remote positions.

Conclusions:

  • Remote C-H functionalization via larger metalacycles presents new retrosynthetic opportunities.
  • Further research is needed to overcome limitations and fully realize the synthetic potential of these challenging reactions.