Synthesis of Complex Phenols Enabled by a Rationally Designed Hydroxide Surrogate

The conversion of aryl halides to phenols under mild reaction conditions is a longstanding and formidable challenge in organic chemistry. Herein, we report the rational design of a broadly applicable Pd‐catalyzed method to prepare phenols with benzaldehyde oxime as a hydroxide surrogate. These react...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2017-04, Vol.56 (16), p.4478-4482
Main Authors: Fier, Patrick S., Maloney, Kevin M.
Format: Article
Language:English
Subjects:
Aromatic compounds
Benzaldehyde
cross-coupling
Halides
Hydroxylation
medicinal chemistry
Organic chemistry
palladium
Phenols
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Summary:The conversion of aryl halides to phenols under mild reaction conditions is a longstanding and formidable challenge in organic chemistry. Herein, we report the rational design of a broadly applicable Pd‐catalyzed method to prepare phenols with benzaldehyde oxime as a hydroxide surrogate. These reactions occur under mildly basic conditions and enable the late‐stage hydroxylation of several functionally‐dense drug‐like aryl halides. The conversion of aryl halides to phenols under mild reaction conditions is a longstanding and formidable challenge in organic chemistry. The rational design of a broadly applicable Pd‐catalyzed method to prepare phenols with benzaldehyde oxime as a hydroxide surrogate is now reported. These reactions occur under mildly basic conditions and enable the late‐stage hydroxylation of functionally dense aryl halides.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201700244