Suzuki Cross-Coupling work-up question

In summary, the conversation is about a Suzuki Cross Coupling reaction using the paper "Nickel-Catalyzed SuzukiMiyaura Couplings in Green Solvents." The reaction involves a bromo-aryl reacting with a boronic acid in heated t-amyl alcohol with the presence of NiCl2(PCy3)2 and tripotassium phosphate. During the work-up, the solvent is transferred into a test tube of 1M HCl, and the product is supposed to be in the aqueous layer. However, the person is unsure how a biphenyl product would dissolve in the aqueous layer and asks for clarification. They also ask if there are any organic molecules that are soluble in 1M HCl and what
  • #1
worryingchem
41
1
Hi, in class I'm doing a Suzuki Cross Coupling reaction based on
"Nickel-Catalyzed SuzukiMiyaura
Couplings in Green Solvents" by Stephen D. Ramgren, Liana Hie, Yuxuan Ye, and Neil K. Garg.
The reaction involved the bromo-aryl reacting with the boronic acid in heated t-amyl alcohol in the presence of NiCl2(PCy3)2 and tripotassium phosphate.

During the work-up, the first thing we did was transferred our solvent into a test tube of 1M HCl. The product is supposed to be in the aqueous layer, but I don't know how a biphenyl product would dissolve in the aqueous layer.
Can someone clear this up for me? Thank you.
suzuki rx.JPG
 
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  • #2
Can you think of any organic molecules that are soluble in 1M HCl?
What are R1 and R2?
 

Related to Suzuki Cross-Coupling work-up question

1. What is Suzuki Cross-Coupling work-up?

Suzuki Cross-Coupling work-up is a type of chemical reaction where two organic compounds are joined together through a palladium-catalyzed cross-coupling reaction. This reaction is commonly used in organic synthesis to create carbon-carbon bonds.

2. What is the purpose of Suzuki Cross-Coupling work-up?

The purpose of Suzuki Cross-Coupling work-up is to create new carbon-carbon bonds in a controlled and efficient manner. This allows for the synthesis of complex organic molecules that are important in pharmaceuticals, materials, and other industries.

3. How is Suzuki Cross-Coupling work-up performed?

Suzuki Cross-Coupling work-up is typically performed by combining two organic compounds, a boronic acid and an organic halide, in the presence of a palladium catalyst and a base. The reaction is typically carried out in an organic solvent at room temperature or under mild heating conditions.

4. What are the advantages of Suzuki Cross-Coupling work-up?

Suzuki Cross-Coupling work-up has several advantages, including high selectivity, mild reaction conditions, and compatibility with a wide range of functional groups. It also allows for the synthesis of complex molecules in a relatively short period of time.

5. What are the limitations of Suzuki Cross-Coupling work-up?

Some limitations of Suzuki Cross-Coupling work-up include the use of expensive palladium catalysts, the need for precise reaction conditions, and the potential for side reactions to occur. Additionally, this reaction may not be suitable for certain types of molecules or functional groups.

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