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Related Concept Videos

Crossed Aldol Reactions: Overview01:04

Crossed Aldol Reactions: Overview

Crossed aldol addition is the reaction between two different carbonyl compounds under acidic or basic conditions. Here, both the carbonyl compounds function as nucleophiles and electrophiles. As shown in Figure 1, such a reaction yields a mixture of products, two of which are formed via self-condensation, while the remaining two are formed via crossed-condensation. Without adjustment, the reaction's usefulness in organic chemistry is decreased.
Coupled Reactions01:17

Coupled Reactions

Cellular processes such as building and breaking down complex molecules occur through stepwise chemical reactions. Some of these chemical reactions are spontaneous and release energy, whereas others require energy to proceed. Cells often couple the energy-releasing reaction with the energy-requiring one to carry out important cell functions. 
Energy in adenosine triphosphate or ATP molecules is easily accessible to do work. ATP powers the majority of energy-requiring cellular reactions. Cells...
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...
Crossed Aldol Reaction Using Weak Bases01:14

Crossed Aldol Reaction Using Weak Bases

This lesson deals with the crossed aldol reaction using weak bases. The self-condensation of an aldehyde having α hydrogen is prevented by adding it slowly to a mixture of formaldehyde and weak bases like hydroxide and alkoxide. Upon slow addition of the aldehyde, the base deprotonates the α carbon of the aldehyde to form the corresponding enolate. The enolate subsequently attacks the formaldehyde to form a single crossed product. Figure 1 depicts the aforementioned reaction.
Crossed Aldol Reaction Using Strong Bases: Directed Aldol Reaction00:56

Crossed Aldol Reaction Using Strong Bases: Directed Aldol Reaction

The reaction between two different carbonyl compounds comprising α hydrogen in the presence of a strong base like lithium diisopropylamide (LDA) to form a crossed aldol product is known as a directed aldol reaction. The directed aldol reaction is depicted in Figure 1.
Phase II Reactions: Miscellaneous Conjugation Reactions01:19

Phase II Reactions: Miscellaneous Conjugation Reactions

Phase II biotransformations are detoxification mechanisms that conjugate xenobiotics with endogenous substances, neutralizing their toxicity.
A key example involves the conjugation of cyanide ions, which impair cellular respiration and alter hemoglobin into non-oxygen-carrying cyanmethemoglobin. To neutralize this threat, a sulfur atom from thiosulphate is transferred to the cyanide ion, catalyzed by the enzyme rhodanese, resulting in an inactive compound called thiocyanate. The production of...

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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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Published on: March 20, 2014

A versatile protocol for Stille-Migita cross coupling reactions.

Alois Fürstner1, Jacques-Alexis Funel, Martin Tremblay

  • 1Max-Planck-Institut für Kohlenforschung, D-45470, Mülheim/Ruhr, Germany. fuerstner@mpi-muelheim.mpg.de

Chemical Communications (Cambridge, England)
|June 21, 2008
PubMed
Summary

A new fluoride-free Stille-Migita reaction protocol using palladium tetrakis(triphenylphosphine) (Pd(PPh3)4), copper thiophene-2-carboxylate (CuTC), and tetrabutylammonium diphenylphosphinate ([Ph2PO2][NBu4]) enables high-yield synthesis. This method preserves sensitive O-silyl and C-silyl groups, expanding its utility in organic synthesis.

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Area of Science:

  • Organic Chemistry
  • Organometallic Chemistry
  • Synthetic Methodology

Background:

  • The Stille-Migita reaction is a valuable carbon-carbon bond-forming reaction.
  • Traditional Stille-Migita protocols often require fluoride sources, which can interfere with silyl-protected functional groups.
  • Developing fluoride-free conditions is crucial for preserving sensitive substrates in complex molecule synthesis.

Purpose of the Study:

  • To develop a novel, high-yielding, and fluoride-free protocol for the Stille-Migita reaction.
  • To demonstrate the compatibility of the new method with silyl-protected functional groups.
  • To expand the scope of the Stille-Migita reaction for challenging synthetic transformations.

Main Methods:

  • Utilized catalytic amounts of palladium tetrakis(triphenylphosphine) ([Pd(PPh3)4]) as the palladium source.
  • Employed copper thiophene-2-carboxylate (CuTC) as a co-catalyst.
  • Incorporated tetrabutylammonium diphenylphosphinate ([Ph2PO2][NBu4]) as an additive in a fluoride-free system.

Main Results:

  • Achieved high yields in a series of demanding Stille-Migita reactions.
  • Successfully preserved a variety of O-silyl and C-silyl groups due to the absence of fluoride ions.
  • Demonstrated the robustness and efficiency of the developed catalytic system.

Conclusions:

  • The combination of [Pd(PPh3)4], CuTC, and [Ph2PO2][NBu4] provides an effective fluoride-free Stille-Migita reaction.
  • This protocol offers a significant advantage for synthesizing molecules containing silyl ethers and silyl-protected carbons.
  • The developed methodology broadens the applicability of the Stille-Migita reaction in modern organic synthesis.