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Lewis Acid–Base Interaction‐Controlled ortho ‐Selective C−H Borylation of Aryl Sulfides
Author(s) -
Li Hong Liang,
Kuninobu Yoichiro,
Kanai Motomu
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201610041
Subject(s) - borylation , chemistry , regioselectivity , lewis acids and bases , aryl , substrate (aquarium) , ligand (biochemistry) , combinatorial chemistry , iridium , catalysis , medicinal chemistry , selectivity , stereochemistry , organic chemistry , biochemistry , alkyl , oceanography , receptor , geology
Abstract 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.