TY - JOUR
T1 - Iron-Catalyzed Oxidative Cross-Coupling of Phenols and Tyrosine Derivatives with 3-Alkyloxindoles
AU - Mintz, Tomer
AU - More, Nagnath Yadav
AU - Gaster, Eden
AU - Pappo, Doron
N1 - Funding Information:
The authors would like to thank the COST-CHAOS organization for funding the participation of N.Y.M., E.G., and D.P. in their conferences. This work was supported by the Israel Science Foundation (grant number 655/20).
Publisher Copyright:
© 2021 American Chemical Society
PY - 2021/12/17
Y1 - 2021/12/17
N2 - In this study, a novel iron-catalyzed oxidative cross-coupling reaction between phenols and 3-alkyloxindole derivatives is reported. The efficient method, which is based on the FeCl3 catalyst and the t-BuOOt-Bu oxidant in 1,2-dichloroethane at 70 °C, affords 3-alkyl-3-(hydroxyaryl)oxindole compounds with a high degree of selectivity. The generality of the conditions was proven by reacting various substituted phenols, naphthols, and tyrosine derivatives with 3-alkyloxindoles. To apply the chemistry for the conjugation of tyrosine-containing short peptides with oxindolylalanine (Oia) derivatives, the reaction conditions were modified [Fe(O2CCF3)3 catalyst, t-BuOOt-Bu, HFIP, 70 °C], and amino acids with acid-stable N-protecting groups were used.
AB - In this study, a novel iron-catalyzed oxidative cross-coupling reaction between phenols and 3-alkyloxindole derivatives is reported. The efficient method, which is based on the FeCl3 catalyst and the t-BuOOt-Bu oxidant in 1,2-dichloroethane at 70 °C, affords 3-alkyl-3-(hydroxyaryl)oxindole compounds with a high degree of selectivity. The generality of the conditions was proven by reacting various substituted phenols, naphthols, and tyrosine derivatives with 3-alkyloxindoles. To apply the chemistry for the conjugation of tyrosine-containing short peptides with oxindolylalanine (Oia) derivatives, the reaction conditions were modified [Fe(O2CCF3)3 catalyst, t-BuOOt-Bu, HFIP, 70 °C], and amino acids with acid-stable N-protecting groups were used.
UR - http://www.scopus.com/inward/record.url?scp=85121025724&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.1c02435
DO - 10.1021/acs.joc.1c02435
M3 - Article
C2 - 34881564
AN - SCOPUS:85121025724
SN - 0022-3263
VL - 86
SP - 18164
EP - 18178
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 24
ER -