Pd-Catalyzed Suzuki-Miyaura Cross-Coupling of Pentafluorophenyl Esters
Abstract
:1. Introduction
2. Results
3. Discussion
4. Materials and Methods
4.1. General Information
4.2. General Procedure for Cross-Coupling of Pentafluorophenyl Esters
4.3. Representative Procedure for Cross-Coupling of Pentafluorophenyl Esters
4.4. Characterization Data for Products 3a–3k (Figures 1 and 2)
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
References
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Sample Availability: Not available. |
Entry | Catalyst | Ligand | Base | [Pd]:L | Yield (%) |
---|---|---|---|---|---|
1 | Pd(OAc)2 | PCy3HBF4 | Na2CO3 | 1:4 | 52 |
2 | Pd(OAc)2 | PCy3HBF4 | KHCO3 | 1:4 | 53 |
3 | Pd(OAc)2 | PCy3HBF4 | NaHCO3 | 1:4 | 30 |
4 | Pd(OAc)2 | PCy3HBF4 | K2CO3 | 1:4 | 12 |
5 | Pd(OAc)2 | PCy3HBF4 | K3PO4 | 1:4 | 47 |
6 | Pd(OAc)2 | PCy3HBF4 | KF | 1:4 | 56 |
7 | Pd(OAc)2 | PPhCy2 | Na2CO3 | 1:4 | 60 |
8 | Pd(OAc)2 | PPh2Cy | Na2CO3 | 1:4 | 5 |
9 | Pd(OAc)2 | PPh3 | Na2CO3 | 1:4 | 5 |
10 | Pd(OAc)2 | DPPB | Na2CO3 | 1:4 | 13 |
11 | Pd(OAc)2 | Xantphos | Na2CO3 | 1:4 | <5 |
12 | Pd(OAc)2 | Pt-Bu3HBF4 | Na2CO3 | 1:4 | <5 |
13 | Pd(dba)2 | PCy3HBF4 | Na2CO3 | 1:4 | 23 |
14 | PdCl2 | PCy3HBF4 | Na2CO3 | 1:4 | 25 |
15 | Pd2(dba)3 | PCy3HBF4 | Na2CO3 | 1:2 | 74 |
16 2 | Pd2(dba)3 | PCy3HBF4 | Na2CO3 | 1:2 | 85 |
17 3 | Pd2(dba)3 | PCy3HBF4 | Na2CO3 | 1:1 | 44 |
18 4 | Pd2(dba)3 | PCy3HBF4 | Na2CO3 | 2:1 | 30 |
19 5 | Pd(OAc)2 | PCy3HBF4 | Na2CO3 | 1:4 | 83 |
20 5 | Pd2(dba)3 | PCy3HBF4 | Na2CO3 | 1:2 | 92 |
21 6 | Pd2(dba)3 | PCy3HBF4 | Na2CO3 | 1:2 | 75 |
22 7 | Pd2(dba)3 | PCy3HBF4 | Na2CO3 | 1:2 | 89 |
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Buchspies, J.; J. Pyle, D.; He, H.; Szostak, M. Pd-Catalyzed Suzuki-Miyaura Cross-Coupling of Pentafluorophenyl Esters. Molecules 2018, 23, 3134. https://doi.org/10.3390/molecules23123134
Buchspies J, J. Pyle D, He H, Szostak M. Pd-Catalyzed Suzuki-Miyaura Cross-Coupling of Pentafluorophenyl Esters. Molecules. 2018; 23(12):3134. https://doi.org/10.3390/molecules23123134
Chicago/Turabian StyleBuchspies, Jonathan, Daniel J. Pyle, Huixin He, and Michal Szostak. 2018. "Pd-Catalyzed Suzuki-Miyaura Cross-Coupling of Pentafluorophenyl Esters" Molecules 23, no. 12: 3134. https://doi.org/10.3390/molecules23123134