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Related Concept Videos

Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
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.
Limitations of Friedel–Crafts Reactions01:26

Limitations of Friedel–Crafts Reactions

Several restrictions limit the use of Friedel–Crafts reactions. First, the halogen in the alkyl halide must be attached to an sp3-hybridized carbon for the Friedel–Crafts reactions to occur. Vinyl or aryl halides do not react since the carbocations formed are unstable under the reaction conditions. Second, Friedel–Crafts alkylation is susceptible to carbocation rearrangement, and the major products obtained have a rearranged carbon skeleton. In contrast, the acylium ion is stabilized by...
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions
11:44

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

Published on: March 20, 2014

Alkenyl Fluorosulfates-Expedient Partners for Palladium-Catalyzed Cross-Coupling Reactions.

Vladyslav Hnativ1,2, Serhii Aleksandrenko1,2, Serhii Zhersh1,2

  • 1Enamine Ltd., Kyїv, Ukraine.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|May 9, 2026
PubMed
Summary

Alkenyl fluorosulfates offer a new, effective alternative for palladium-catalyzed cross-coupling reactions. These compounds demonstrate comparable or superior reactivity to traditional triflates and halides in various coupling methods.

Keywords:
building blockscoupling reactionsenolatesfluorosulfatespalladium

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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

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Scaled-Up Preparation of an Intermediate of Upatinib, ACT051-3
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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions
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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions

Published on: March 20, 2014

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

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Scaled-Up Preparation of an Intermediate of Upatinib, ACT051-3
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Scaled-Up Preparation of an Intermediate of Upatinib, ACT051-3

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Area of Science:

  • Organic Chemistry
  • Catalysis

Background:

  • Palladium-catalyzed cross-coupling reactions are vital in organic synthesis.
  • Triflates and halides are common coupling partners, but alternatives are sought.
  • Alkenyl fluorosulfates present a potential new class of coupling reagents.

Purpose of the Study:

  • To evaluate alkenyl fluorosulfates as coupling partners in palladium-catalyzed reactions.
  • To develop efficient synthesis methods for alkenyl fluorosulfates.
  • To compare the reactivity of alkenyl fluorosulfates with existing coupling reagents like triflates and halides.

Main Methods:

  • Synthesis of alkenyl fluorosulfates via reaction of carbonyl compounds with sulfuryl fluoride (SO2F2).
  • Evaluation of reactivity in Suzuki, Sonogashira, Heck, Stille, and Buchwald-Hartwig cross-coupling reactions.
  • Assessment of performance in Miyaura borylation reactions.

Main Results:

  • Efficient multigram synthesis protocols for alkenyl fluorosulfates were established.
  • Alkenyl fluorosulfates showed good reactivity in various palladium-catalyzed cross-coupling reactions.
  • Their reactivity was found to be similar or higher than that of alkenyl triflates.
  • Limitations of the methods were identified.

Conclusions:

  • Alkenyl fluorosulfates are viable and effective coupling partners in palladium-catalyzed reactions.
  • They serve as a valuable alternative to traditional triflates and halides.
  • The developed synthesis and coupling protocols offer new synthetic possibilities.