Achiral CpxIr(III)/Chiral Carboxylic Acid
Catalyzed Enantioselective C–H Amidation of Ferrocenes under
Mild Conditions
Posted on 2020-06-17 - 13:03
Ir(III)-catalyzed
enantioselective C–H activation generally
relies on the combination of chiral Ir(III) cyclopentadienyl complexes
with chiral carboxylic acids to ensure high enantiocontrol. We report
herein the achiral CpxIr(III)-catalyzed enantioselective
C–H amidation of ferrocenes. Crucial to the high enantioselectivity
is the use of a chiral carboxylic acid ligand derived from tert-leucine via Pd(II)-catalyzed γ-C(sp3)–H arylation and a sterically more hindered CpxIr(III) catalyst. This reaction proceeds smoothly under very mild
conditions (0 °C) and tolerates a wide range of ferrocene carboxamides
and dioxazolones, providing the amidation products in good yields
with high enantioselectivity (up to 97.5:2.5 er). This protocol might
open the way for achiral CpxIr(III)-catalyzed asymmetric
C–H activation.
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Liu, Lei; Song, Hong; Liu, Yan-Hua; Wu, Le-Song; Shi, Bing-Feng (2020). Achiral CpxIr(III)/Chiral Carboxylic Acid
Catalyzed Enantioselective C–H Amidation of Ferrocenes under
Mild Conditions. ACS Publications. Collection. https://doi.org/10.1021/acscatal.0c02049
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AUTHORS (5)
LL
Lei Liu
HS
Hong Song
YL
Yan-Hua Liu
LW
Le-Song Wu
BS
Bing-Feng Shi