TY - JOUR
T1 - Significant enhancement in the efficiency and selectivity of iron-catalyzed oxidative cross-coupling of phenols by fluoroalcohols
AU - Gaster, Eden
AU - Vainer, Yulia
AU - Regev, Almog
AU - Narute, Sachin
AU - Sudheendran, Kavitha
AU - Werbeloff, Aviya
AU - Shalit, Hadas
AU - Pappo, Doron
N1 - Publisher Copyright:
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
PY - 2015/3/27
Y1 - 2015/3/27
N2 - Significant enhancement of both the rate and the chemoselectivity of iron-catalyzed oxidative coupling of phenols can be achieved in fluorinated solvents, such as 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP), 2,2,2-trifluoroethanol (TFE), and 1-phenyl-2,2,2-trifluoroethanol. The generality of this effect was examined for the cross-coupling of phenols with arenes and polycyclic aromatic hydrocarbons (PAHs) and of phenol with β-dicarbonyl compounds. The new conditions were utilized in the synthesis of 2-dehydroxycalodenin B in only four synthetic steps. Not just a solvent: The use of fluorinated solvents leads to a significant rate acceleration and enhancement of the chemoselectivity of the iron-catalyzed oxidative coupling of phenols. This method was used for the synthesis of 2-dehydroxycalodenin B.
AB - Significant enhancement of both the rate and the chemoselectivity of iron-catalyzed oxidative coupling of phenols can be achieved in fluorinated solvents, such as 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP), 2,2,2-trifluoroethanol (TFE), and 1-phenyl-2,2,2-trifluoroethanol. The generality of this effect was examined for the cross-coupling of phenols with arenes and polycyclic aromatic hydrocarbons (PAHs) and of phenol with β-dicarbonyl compounds. The new conditions were utilized in the synthesis of 2-dehydroxycalodenin B in only four synthetic steps. Not just a solvent: The use of fluorinated solvents leads to a significant rate acceleration and enhancement of the chemoselectivity of the iron-catalyzed oxidative coupling of phenols. This method was used for the synthesis of 2-dehydroxycalodenin B.
KW - cross-dehydrogenative coupling
KW - fluorinated solvents
KW - iron catalysis
KW - oxidative cross-coupling
KW - phenols
UR - http://www.scopus.com/inward/record.url?scp=85027931487&partnerID=8YFLogxK
U2 - 10.1002/anie.201409694
DO - 10.1002/anie.201409694
M3 - Article
AN - SCOPUS:85027931487
SN - 1433-7851
VL - 54
SP - 4198
EP - 4202
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 14
ER -