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CHEM333 (RBL) > 8. Suzuki Miyaura > Flashcards

8. Suzuki Miyaura Flashcards

1
Q

What type of coupling does the Suzuki reaction primarily involve?

A

sp-sp couplings between aromatic rings

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2
Q

What agrochemical is produced using Suzuki coupling as the first step?

A

Boscalid

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3
Q

What is a common coupling partner in Suzuki reactions?

A

Boronic acids

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4
Q

Why are boronic acids commonly used in Suzuki reactions?

A

They are mostly air-stable crystalline solids and many are commercially available

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5
Q

What is a disadvantage of using boronic acids in Suzuki reactions?

A

They don’t give sharp spots on TLC and their solution chemistry is complicated

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6
Q

Name two alternative boron compounds used in Suzuki reactions.

A
  • Cyclic borate esters (R-Bpin, R-Bcat)
  • Trifluoroborates
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7
Q

How do some alternative boron compounds work in Suzuki reactions?

A

They hydrolyze slowly to boronic acid in situ

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8
Q

What is the selectivity observed in reactions involving 2,4-dichloropyrimidine?

A

Iodine is substituted in preference to bromine

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9
Q

What is the role of palladium (Pd) in Suzuki reactions?

A

Catalyst

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10
Q

True or False: Suzuki reactions can also occur between sp²-sp’ vinyl centers.

A

True

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11
Q

What is retained during Suzuki reactions involving double bonds?

A

Stereochemistry of the double bonds

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12
Q

What type of biaryls can be prepared through Suzuki reactions?

A

Hindered biaryls

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13
Q

Fill in the blank: The reaction of R-Br with (HO)B.R is part of the __________ process.

A

Suzuki-Miyaura coupling

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14
Q

What is the temperature and solvent used for the synthesis of Pacritinib in Suzuki reactions?

A

89 °C, dimethoxyethane/H2O

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15
Q

What is the yield percentage for the synthesis of Erdafitinib in Suzuki reactions?

A

82%

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16
Q

What is the first step in the catalytic cycle of the Buchwald-Harwig amination mechanism?

A

Oxidative addition

The oxidative addition is usually the slowest step.

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17
Q

What is the term used when an organometallic group is transferred from one metal atom to another in the catalytic cycle?

A

Transmetallation

This involves transferring an organometallic group from one metal atom (e.g., boron) to another (e.g., palladium).

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18
Q

In the context of the catalytic cycle, what happens during reductive elimination?

A

Formation of the final product by releasing the metal complex

This step involves the elimination of the product while regenerating the catalyst.

19
Q

What reactants are typically made from aryl halides in the organometallic route?

A

Organolithium or Grignard reagents

Aryl halides are converted into organometallics before being added to boronic acids.

20
Q

What is a limitation of the organometallic route in synthesizing boronic acids?

A

The reagents cannot contain any functional groups incompatible with organolithiums or Grignards

This restricts the range of functional groups that can be used.

21
Q

What is the starting material in the Miyaura borylation reaction?

A

Aryl halide

This reaction attaches the boron group as a boronate ester using Pd catalysis.

22
Q

In Miyaura borylation, what does the transmetallation step break instead of a C-B bond?

A

B-B bond

This step differentiates it from the Suzuki reaction.

23
Q

What type of bases work best in the Miyaura borylation?

A

Lipophile carboxylates

Acetate is noted as less effective compared to lipophile carboxylates.

24
Q

Fill in the blank: The oxidative addition is usually the ______ step in the catalytic cycle.

A

slowest

25
Q

True or False: The R-Bpin produced in the Miyaura borylation can react with the aryl halide from which it was formed.

A

True

This reaction can lead to side products if not controlled.

26
Q

What is formed when the anionic ate complex initially created in the organometallic route hydrolyzes?

A

Boronic acid

This occurs during aqueous workup.

27
Q

What is the role of the carboxylate base in the Miyaura borylation?

A

To reduce side reactions

It reduces the chances of the R-Bpin reacting with the aryl halide.

28
Q

What reaction is particularly useful for coupling two aryl halides?

A

Borylation followed by Suzuki coupling

This method allows for effective coupling of two aryl halides.

29
Q

What is the first step in the sequential reactions for coupling aryl halides?

A

Miyaura borylation

This step is often followed by Suzuki coupling.

30
Q

What is the second step in the sequential reactions for coupling aryl halides?

A

Suzuki coupling

This step typically occurs after the Miyaura borylation.

31
Q

What term describes the process of performing two reactions sequentially in the same pot?

A

Telescoping

This method is used when the reaction conditions are sufficiently similar.

32
Q

What is the role of PdCl2 in the reaction mixture?

A

Catalyst

PdCl2 is used as a catalyst for the coupling reactions.

33
Q

What base is often used in the Suzuki coupling reaction after borylation?

A

Different base

The specific base may vary depending on the reaction conditions.

34
Q

True or False: The reaction mixture in these coupling reactions is typically homogeneous.

A

False

The reaction mixture is probably heterogeneous.

35
Q

What is a common coupling partner in these reactions?

A

Aryl halides

Other partners may include triflates or carbonyl compounds.

36
Q

What is triflate (OTf) often considered in coupling reactions?

A

Pseudohalogen

It is roughly equivalent to bromine as a leaving group.

37
Q

What is used to make ary triflates?

A

Triflic anhydride or equivalent and base

These are used to produce ary triflates in the first step.

38
Q

Fill in the blank: The triflate is made using _______ as the base in the first step.

A

N-methyl morpholine (NMM)

NMM is a common base used in this process.

39
Q

What type of reaction is used to create vinyl triflates?

A

S_NAr reaction

This reaction is often part of a sequence involving other steps.

40
Q

What is one potential issue when creating vinyl triflates?

A

Regio- and stereochemistry considerations

These aspects may complicate the synthesis and are beyond the basic lectures.

41
Q

What is the purpose of protecting the ketone as an acetal in the synthesis sequence?

A

To stop base-catalyzed side reactions

Protecting groups are commonly used to prevent unwanted reactions.

42
Q

What reagent is mentioned as being used for creating vinyl triflates?

A

Lithium reagents

These reagents are useful in various synthetic steps.

43
Q

What is the temperature condition mentioned for one of the reactions?

A

100 °C

Specific temperatures are crucial for optimizing reaction conditions.

CHEM333 (RBL) (7 decks)

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