TY - JOUR
T1 - Chiral Bis-8-Aryl-isoquinoline Bis-alkylamine Iron Catalysts for Asymmetric Oxidation Reactions
AU - Mintz, Tomer
AU - Liu, Lei
AU - Pappo, Doron
N1 - Publisher Copyright:
© 2025 The Authors. Published by American Chemical Society.
PY - 2025/1/1
Y1 - 2025/1/1
N2 - A novel class of bis-8-aryl-isoquinoline (AriQ) bis-alkylamine iron complexes, FeII(AriQ2dp)(OTf)2 and FeII(AriQ2mc)(OTf)2 (dp = dipyrrolidinyl or mc = N,N′-dimethylcyclohexyl-diamine), for asymmetric oxidation reactions is reported. The scalable divergent synthesis of 8-aryl-3-formylisoquinolines (8), the key intermediates in preparing these ligands, enables precise structural and electronic tuning around the metal center. The enantioselective epoxidation and hydroxy carbonylation of conjugated alkenes, mediated by the FeII(3,5-di-CF3iQ2dp) catalyst with H2O2 as the oxidant, demonstrates the potential of these redox FeII[N4] catalysts in inducing face selection in oxygen transfer transformations.
AB - A novel class of bis-8-aryl-isoquinoline (AriQ) bis-alkylamine iron complexes, FeII(AriQ2dp)(OTf)2 and FeII(AriQ2mc)(OTf)2 (dp = dipyrrolidinyl or mc = N,N′-dimethylcyclohexyl-diamine), for asymmetric oxidation reactions is reported. The scalable divergent synthesis of 8-aryl-3-formylisoquinolines (8), the key intermediates in preparing these ligands, enables precise structural and electronic tuning around the metal center. The enantioselective epoxidation and hydroxy carbonylation of conjugated alkenes, mediated by the FeII(3,5-di-CF3iQ2dp) catalyst with H2O2 as the oxidant, demonstrates the potential of these redox FeII[N4] catalysts in inducing face selection in oxygen transfer transformations.
UR - http://www.scopus.com/inward/record.url?scp=85216390660&partnerID=8YFLogxK
U2 - 10.1021/acs.orglett.5c00050
DO - 10.1021/acs.orglett.5c00050
M3 - Article
C2 - 39841035
AN - SCOPUS:85216390660
SN - 1523-7060
JO - Organic Letters
JF - Organic Letters
ER -