Abstract
Decarboxylative coupling reactions of alkynyl carboxylic acids with aryl tosylates were developed in the presence of a palladium catalyst. Among the commercially available phosphine ligands, only 1-dicyclohexylphosphino-2-(di-tert-butylphosphino-ethyl)ferrocene (CyPF-tBu) showed good reactivity. The reaction took place smoothly and gave the decarboxylative coupled products in moderate to good yields. This demonstrates the excellent functional group tolerance toward alkyl, alkoxy, fluoro, thiophenyl, ester, and ketone groups. In addition, alkyl-substituted propiolic acids, such as octynoic and hexynoic acids, were coupled with phenyl tosylate to provide the desired products. We found that the electronic properties of the substituents on the phenyl ring in arylpropiolic acids are an important factor. The order of reactivity was found to be aryl iodide > aryl bromide > aryl tosylate > aryl chloride. However, aryl chloride-bearing electron-withdrawing groups showed higher reactivity than those bearing aryl tosylates.
| Original language | English |
|---|---|
| Pages (from-to) | 6259-6269 |
| Number of pages | 11 |
| Journal | ACS Omega |
| Volume | 2 |
| Issue number | 9 |
| DOIs | |
| Publication status | Published - 2017 Jan 1 |
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ASJC Scopus subject areas
- Chemistry(all)
- Chemical Engineering(all)
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Palladium-Catalyzed Decarboxylative Coupling of Alkynyl Carboxylic Acids with Aryl Tosylates. / Lee, Ju Hyeon; Raja, Gabriel Charles Edwin; Yu, Subeen; Lee, Junseong; Song, Kwang Ho; Lee, Sunwoo.
In: ACS Omega, Vol. 2, No. 9, 01.01.2017, p. 6259-6269.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Palladium-Catalyzed Decarboxylative Coupling of Alkynyl Carboxylic Acids with Aryl Tosylates
AU - Lee, Ju Hyeon
AU - Raja, Gabriel Charles Edwin
AU - Yu, Subeen
AU - Lee, Junseong
AU - Song, Kwang Ho
AU - Lee, Sunwoo
PY - 2017/1/1
Y1 - 2017/1/1
N2 - Decarboxylative coupling reactions of alkynyl carboxylic acids with aryl tosylates were developed in the presence of a palladium catalyst. Among the commercially available phosphine ligands, only 1-dicyclohexylphosphino-2-(di-tert-butylphosphino-ethyl)ferrocene (CyPF-tBu) showed good reactivity. The reaction took place smoothly and gave the decarboxylative coupled products in moderate to good yields. This demonstrates the excellent functional group tolerance toward alkyl, alkoxy, fluoro, thiophenyl, ester, and ketone groups. In addition, alkyl-substituted propiolic acids, such as octynoic and hexynoic acids, were coupled with phenyl tosylate to provide the desired products. We found that the electronic properties of the substituents on the phenyl ring in arylpropiolic acids are an important factor. The order of reactivity was found to be aryl iodide > aryl bromide > aryl tosylate > aryl chloride. However, aryl chloride-bearing electron-withdrawing groups showed higher reactivity than those bearing aryl tosylates.
AB - Decarboxylative coupling reactions of alkynyl carboxylic acids with aryl tosylates were developed in the presence of a palladium catalyst. Among the commercially available phosphine ligands, only 1-dicyclohexylphosphino-2-(di-tert-butylphosphino-ethyl)ferrocene (CyPF-tBu) showed good reactivity. The reaction took place smoothly and gave the decarboxylative coupled products in moderate to good yields. This demonstrates the excellent functional group tolerance toward alkyl, alkoxy, fluoro, thiophenyl, ester, and ketone groups. In addition, alkyl-substituted propiolic acids, such as octynoic and hexynoic acids, were coupled with phenyl tosylate to provide the desired products. We found that the electronic properties of the substituents on the phenyl ring in arylpropiolic acids are an important factor. The order of reactivity was found to be aryl iodide > aryl bromide > aryl tosylate > aryl chloride. However, aryl chloride-bearing electron-withdrawing groups showed higher reactivity than those bearing aryl tosylates.
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UR - http://www.scopus.com/inward/citedby.url?scp=85042188377&partnerID=8YFLogxK
U2 - 10.1021/acsomega.7b01165
DO - 10.1021/acsomega.7b01165
M3 - Article
AN - SCOPUS:85042188377
VL - 2
SP - 6259
EP - 6269
JO - ACS Omega
JF - ACS Omega
SN - 2470-1343
IS - 9
ER -