期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 56, 期 6, 页码 1495-1499出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201610041
关键词
borylation; C-H activation; Lewis acid-base interactions; noncovalent bonding; ortho-selectivity
资金
- ERATO from JST
- Ministry of Education, Culture, Sports, Science, and Technology of Japan
- Grants-in-Aid for Scientific Research [26288014] Funding Source: KAKEN
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.
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