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Decarboxylative C(sp 3 )−O Cross‐Coupling
Author(s) -
Mao Runze,
Balon Jonathan,
Hu Xile
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201808024
Subject(s) - alkyl , aryl , electrophile , chemistry , phenols , catalysis , organic chemistry , functional group , combinatorial chemistry , medicinal chemistry , polymer
Abstract Alkyl aryl ethers are an important class of compounds in medicinal and agricultural chemistry. Catalytic C(sp 3 )−O cross‐coupling of alkyl electrophiles with phenols is an unexplored disconnection strategy to the synthesis of alkyl aryl ethers, with the potential to overcome some of the major limitations of existing methods such as C(sp 2 )−O cross‐coupling and S N 2 reactions. Reported here is a tandem photoredox and copper catalysis to achieve decarboxylative C(sp 3 )−O coupling of alkyl N ‐hydroxyphthalimide (NHPI) esters with phenols under mild reaction conditions. This method was used to synthesize a diverse set of alkyl aryl ethers using readily available alkyl carboxylic acids, including many natural products and drug molecules. Complementarity in scope and functional‐group tolerance to existing methods was demonstrated.