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Synthesis of Ketones by C−H Functionalization of Aldehydes with Boronic Acids under Transition‐Metal‐Free Conditions
Author(s) -
Roscales Silvia,
Csáky Aurelio G.
Publication year - 2021
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.202015835
Subject(s) - chemistry , iminium , boronic acid , aldehyde , intramolecular force , surface modification , nitrosobenzene , reagent , transition metal , combinatorial chemistry , organic chemistry , metalation , catalysis
A method for the synthesis of ketones from aldehydes and boronic acids via a transition‐metal‐free C−H functionalization reaction is reported. The method employs nitrosobenzene as a reagent to drive the simultaneous activation of the boronic acid as a boronate and the activation of the C−H bond of the aldehyde as an iminium species that triggers the key C−C bond‐forming step via an intramolecular migration from boron to carbon. These findings constitute a practical, scalable, and operationally straightforward method for the synthesis of ketones.