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Lewis Acid–Base Interaction‐Controlled ortho‐Selective C−H Borylation of Aryl Sulfides

An iridium/bipyridine‐catalyzed ortho‐selective C−H borylation of aryl sulfides was developed. High ortho‐selectivity was achieved by a Lewis acid–base interaction between a boryl group of the ligand and a sulfur atom of the substrate. This is the first example of a catalytic and regioselective C−H...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2017-02, Vol.56 (6), p.1495-1499
Main Authors: Li, Hong Liang, Kuninobu, Yoichiro, Kanai, Motomu
Format: Article
Language:English
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Summary:An iridium/bipyridine‐catalyzed ortho‐selective C−H borylation of aryl sulfides was developed. High ortho‐selectivity was achieved by a Lewis acid–base interaction between a boryl group of the ligand and a sulfur atom of the substrate. This is the first example of a catalytic and regioselective C−H transformation controlled by a Lewis acid–base interaction between a ligand and a substrate. The C−H borylation reaction could be conducted on a gram scale, and with a bioactive molecule as a substrate, demonstrating its applicability to late‐stage regioselective C−H borylation. A bioactive molecule was synthesized from an ortho‐borylated product by converting the boryl and methylthio groups of the product. An iridium/bipyridine‐catalyzed ortho‐selective C−H borylation of aryl sulfides has been developed. High ortho‐selectivity was achieved by a Lewis acid–base interaction between a ligand boryl group and a substrate sulfur atom. This is the first example of a catalytic and regioselective C−H transformation controlled by a Lewis acid–base interaction between ligand and substrate.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201610041