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Related Concept Videos

Acid-Catalyzed Ring-Opening of Epoxides02:24

Acid-Catalyzed Ring-Opening of Epoxides

9.0K
Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
9.0K
Base-Catalyzed Ring-Opening of Epoxides02:26

Base-Catalyzed Ring-Opening of Epoxides

10.2K
Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...
10.2K
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

2.7K
Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
2.7K
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

3.5K
Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
3.5K
Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene01:17

Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene

8.1K
The electrophilic addition of hydrogen halides such as HBr to alkenes and nonconjugated dienes gives a single product as per Markovnikov’s rule.
8.1K
Base-Catalyzed Aldol Addition Reaction01:08

Base-Catalyzed Aldol Addition Reaction

4.6K
As depicted in Figure 1, base-catalyzed aldol addition involves adding two carbonyl compounds in aqueous sodium hydroxide to form a β-hydroxy carbonyl compound.
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Related Experiment Video

Updated: Jan 31, 2026

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

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Palladium-Catalyzed Dearomative syn-1,4-Diamination.

William C Wertjes1, Mikiko Okumura1, David Sarlah1

  • 1Roger Adams Laboratory, Department of Chemistry , University of Illinois , Urbana , Illinois 61801 , United States.

Journal of the American Chemical Society
|December 20, 2018
PubMed
Summary

This study introduces a novel dearomative syn-1,4-diamination method for functionalizing simple arenes and amines. The efficient one-pot protocol provides rapid access to complex molecular building blocks with high selectivity.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Catalysis

Background:

  • Dearomatization strategies are crucial for accessing complex molecular architectures.
  • Developing efficient methods for C-N bond formation remains a key challenge in organic synthesis.

Purpose of the Study:

  • To report a novel dearomative syn-1,4-diamination protocol.
  • To enable the synthesis of complex building blocks from simple arenes and amines.

Main Methods:

  • Visible-light-mediated [4+2]-photocycloaddition to form arene-arenophile para-cycloadducts.
  • Palladium-catalyzed formal allylic substitution with amine nucleophiles.
  • One-pot reaction sequence.

Main Results:

  • Exclusive syn-1,4-diamination selectivity achieved.
  • Enantioselective desymmetrization of naphthalene demonstrated.
  • Elaboration of amine-containing drug molecules enabled.
  • Access to diverse unsaturated products for further functionalization.

Conclusions:

  • The developed method offers a rapid and straightforward route to complex, otherwise inaccessible, building blocks.
  • This dearomative functionalization strategy broadens the scope of arene and amine transformations.
  • The protocol facilitates the synthesis of valuable intermediates for medicinal chemistry and materials science.