TY - JOUR
T1 - Meso-Tetraphenylporphyrin Iron Chloride Catalyzed Selective Oxidative Cross-Coupling of Phenols
AU - Shalit, Hadas
AU - Libman, Anna
AU - Pappo, Doron
N1 - Funding Information:
This research was supported by the Israel Science Foundation (Grant No. 164/16).
Publisher Copyright:
© 2017 American Chemical Society.
PY - 2017/9/27
Y1 - 2017/9/27
N2 - A novel catalytic system for oxidative cross-coupling of readily oxidized phenols with poor nucleophilic phenolic partners based on an iron meso-tetraphenylporphyrin chloride (Fe[TPP]Cl) complex in 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP) was developed. The unique chemoselectivity of this reaction is attributed to the coupling between a liberated phenoxyl radical with an iron-ligated phenolic coupling partner. The conditions are scalable for preparing a long list of unsymmetrical biphenols assembled from a less reactive phenolic unit substituted with alkyl or halide groups.
AB - A novel catalytic system for oxidative cross-coupling of readily oxidized phenols with poor nucleophilic phenolic partners based on an iron meso-tetraphenylporphyrin chloride (Fe[TPP]Cl) complex in 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP) was developed. The unique chemoselectivity of this reaction is attributed to the coupling between a liberated phenoxyl radical with an iron-ligated phenolic coupling partner. The conditions are scalable for preparing a long list of unsymmetrical biphenols assembled from a less reactive phenolic unit substituted with alkyl or halide groups.
UR - http://www.scopus.com/inward/record.url?scp=85030107673&partnerID=8YFLogxK
U2 - 10.1021/jacs.7b05898
DO - 10.1021/jacs.7b05898
M3 - Article
AN - SCOPUS:85030107673
SN - 0002-7863
VL - 139
SP - 13404
EP - 13413
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 38
ER -