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Preparation and Reactions of Sulfides

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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.
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Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

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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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The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
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Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

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Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

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Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
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Cycloaddition Reactions: Overview01:16

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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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Process-Ready Nickel-Catalyzed Suzuki-Miyaura Coupling Enabled by tri-ProPhos.

Jin Yang1, Hengyuan Zhao1, Johnathan E Schultz2

  • 1Department of Chemistry, New York University, 100 Washington Square East, New York, New York 10003, United States.

ACS Catalysis
|November 27, 2025
PubMed
Summary

A novel (tri-ProPhos)Ni catalyst enables efficient nickel-catalyzed Suzuki-Miyaura coupling (Ni-SMC) of heterocycles in greener solvents like alcohols and water, reducing costs for active pharmaceutical ingredient synthesis.

Keywords:
ProPhosSuzuki–Miyauragreen-solventheterocyclesnickelpharmaceutical process synthesis

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Process Chemistry

Background:

  • Palladium-catalyzed Suzuki-Miyaura coupling (Pd-SMC) is crucial for synthesizing active pharmaceutical ingredients (APIs) but is costly.
  • Nickel-catalyzed SMC (Ni-SMC) is a cheaper alternative, yet faces challenges in catalyst loading and substrate scope.
  • There's a need for sustainable synthesis methods using polar solvents like alcohols and water.

Purpose of the Study:

  • To develop a novel catalyst for efficient Ni-SMC of heterocycles in polar solvents.
  • To address limitations of existing Ni-SMC methods regarding catalyst loading and solvent compatibility.
  • To provide a scalable and cost-effective alternative for API synthesis.

Main Methods:

  • Development of a (tri-ProPhos)Ni catalyst featuring a phosphine moiety with hydroxyl groups.
  • Application of the catalyst for Ni-SMC of various heterocycles in isopropanol (i-PrOH) and water.
  • Validation of the catalytic system on a decagram scale.

Main Results:

  • The (tri-ProPhos)Ni catalyst enables robust Ni-SMC of diverse heterocycles, including those found in APIs.
  • Efficient catalysis was achieved in i-PrOH and pure water, demonstrating compatibility with polar solvents.
  • Low catalyst loadings (0.03-0.1 mol %) were effective, and the method was successfully scaled to decagram quantities.

Conclusions:

  • The (tri-ProPhos)Ni catalyst offers a sustainable and efficient platform for Ni-SMC in greener solvents.
  • This method presents a viable alternative to Pd-SMC for commercial API synthesis, reducing costs and environmental impact.
  • The catalyst's unique ligand structure enhances stability and facilitates transmetalation, broadening the scope of Ni-SMC.