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, 83 (1), 469-477

Rapidly Activating Pd-Precatalyst for Suzuki-Miyaura and Buchwald-Hartwig Couplings of Aryl Esters

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Rapidly Activating Pd-Precatalyst for Suzuki-Miyaura and Buchwald-Hartwig Couplings of Aryl Esters

Amira H Dardir et al. J Org Chem.

Abstract

Esters are valuable electrophiles for cross-coupling due to their ubiquity and ease of synthesis. However, harsh conditions are traditionally required for the effective cross-coupling of ester substrates. Utilizing a recently discovered precatalyst, Pd-catalyzed Suzuki-Miyaura and Buchwald-Hartwig reactions involving cleavage of the C(acyl)-O bond of aryl esters that proceed under mild conditions are reported. The Pd(II) precatalyst is highly active because it is reduced to the Pd(0) active species more rapidly than previous precatalysts.

Conflict of interest statement

Notes

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Summary of previous work on cross-coupling reactions of aryl esters and comparison to this work.
Scheme 1
Scheme 1. Isolated Yields of Products in Suzuki–Miyaura Reactions Using Aryl Estersb
aPerformed on 1 mmol scale in relation to benzoate. Yields are the average of two runs. bConditions: aryl ester (0.50 mmol), boronic acid (0.75 mmol), KOH (1.0 mmol), (η3-1-tBu-indenyl)Pd(IPr)(Cl) precatalyst (0.005 mmol), THF (2 mL), water (0.5 mL).
Scheme 2
Scheme 2. Isolated Yields of Products in Buchwald–Hartwig Reactions Using Aryl Esters and 4-Methoxyanilineb
aPerformed on 1 mmol scale in relation to aryl ester. Yields are the average of two runs. bConditions: aryl ester (0.50 mmol), 4-methoxyaniline (0.60 mmol), Cs2CO3 (0.75 mmol), (η3-1-tBu-indenyl)Pd(SIPr)(Cl) precatalyst (0.005 mmol), water (2 mL), THF (0.5 mL).
Scheme 3
Scheme 3. Isolated Yields of Products in Buchwald–Hartwig Reactions Using Phenyl Benzoate and Different Substituted Anilinesb
a2.5 equiv of amine and 3 equiv of Cs2CO3 were utilized. bConditions: aryl ester (0.50 mmol), substituted aniline (0.60 mmol), Cs2CO3 (0.75 mmol), (η3-1-tBu-indenyl)Pd(SIPr)(Cl) precatalyst (0.005 mmol), water (2 mL), THF (0.5 mL). Yields are the average of two runs.

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