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Related Concept Videos

Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

2.0K
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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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

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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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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

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3.2K
The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para...
3.2K
Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate02:21

Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate

14.5K
Alkenes can be dihydroxylated using potassium permanganate.  The method encompasses the reaction of an alkene with a cold, dilute solution of potassium permanganate under basic conditions to form a cis-diol along with a brown precipitate of manganese dioxide.
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Metallaphotoredox catalysis with organic dyes.

Andrea Gualandi1, Michele Anselmi1, Francesco Calogero1

  • 1ALMA MATER STUDIORUM Università di Bologna, Dipartimento di Chimica "G. Ciamician", Via Selmi 2, 40126 Bologna, Italy. piergiorgio.cozzi@unibo.it andrea.gualandi10@unibo.it.

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Organic dyes are expanding their role in photoredox catalysis, enabling new reactions and transformations. Their low cost, tailored synthesis, and integration with metal catalysis drive widespread adoption in organic synthesis.

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Area of Science:

  • Organic Chemistry
  • Photocatalysis
  • Catalysis

Background:

  • Organic dyes are increasingly utilized in photoredox catalysis.
  • Recent reviews highlight their expanding applications.
  • Developments focus on new dye synthesis and catalytic systems.

Purpose of the Study:

  • To review the expanding use of organic dyes in photoredox catalysis.
  • To cover recent advancements in dye-mediated metal-catalyzed processes.
  • To highlight the factors driving the widespread application of organic dyes.

Main Methods:

  • Review of recent literature on organic dyes in photoredox catalysis.
  • Analysis of new dye synthesis and applications.
  • Examination of flow photoredox reactions, stereoselective, and multicomponent transformations.
  • Discussion of metal-catalyzed processes mediated by organic dyes.

Main Results:

  • Organic dyes significantly expand the scope of photoredox catalysis.
  • New dyes enable applications in flow chemistry, stereoselective, and multicomponent reactions.
  • Low cost, tailored synthesis, and theoretical understanding facilitate widespread use.
  • Organic dyes are crucial in metallaphotoredox catalysis.

Conclusions:

  • Organic dyes are a versatile and cost-effective tool in modern organic synthesis.
  • Continued development in dye design and catalytic strategies will further expand their applications.
  • The integration of organic dyes with metal catalysis offers powerful synthetic methodologies.