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ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

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

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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...
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Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

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Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
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meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

6.9K
All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for...
6.9K
Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

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The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
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Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

7.6K
Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
7.6K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.8K
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.
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Heteroatom-Functionalization of Aromatic Rings Using Near Infrared Light-Activatable Catalysts.

Tasuku Iba1, Rinko Kobayashi1, Taniyuki Furuyama2

  • 1Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan.

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This study introduces a new method for functionalizing aromatic rings using near-infrared (NIR) light and a phthalocyanine photocatalyst. The reaction efficiently incorporates heteroatoms like phosphorus, sulfur, and boron onto aromatic structures.

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Area of Science:

  • Organic Chemistry
  • Photochemistry

Background:

  • Near-infrared (NIR) light offers deep tissue penetration, making it ideal for advanced organic synthesis.
  • Developing efficient photocatalysts for NIR-driven reactions is crucial for expanding synthetic capabilities.

Purpose of the Study:

  • To develop a novel method for heteroatom-functionalization of aromatic rings using NIR light.
  • To utilize phthalocyanine-based photocatalysts for generating reactive oxygen species.

Main Methods:

  • Employed phthalocyanine zinc complexes as photocatalysts activated by NIR light.
  • Investigated the generation of aryl radicals from arylhydrazine derivatives via singlet oxygen (1O2).
  • Utilized arylhydrazine hydrochloride for stable and facile incorporation of heteroatoms (P, S, B).

Main Results:

  • Successfully achieved heteroatom incorporation (P, S, B) onto aromatic rings via aryl radical intermediates.
  • Demonstrated selective transformation of fluorescent dyes.
  • Showcased reaction feasibility under shielded conditions, overcoming limitations of conventional photochemistry.

Conclusions:

  • Developed a novel NIR light-driven strategy for aromatic ring functionalization.
  • The method enables efficient and selective heteroatom incorporation using readily available precursors.
  • Offers a versatile platform for organic synthesis, particularly for complex molecules and under challenging conditions.