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
N1 - Funding Information:
This research was supported by the National Research Foundation of Korea (NRF) grant funded by the Korean government (MSIP) (NRF-2015R1A4A1041036 and NRF-2017R1A2B2002929). The spectral data were obtained from the Korea Basic Science Institute, Gwangju Branch.
Publisher Copyright:
© 2017 American Chemical Society.
PY - 2017/9/30
Y1 - 2017/9/30
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.
UR - http://www.scopus.com/inward/record.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 -