Synthesis 2017; 49(21): 4745-4752
DOI: 10.1055/s-0036-1588735
special topic
© Georg Thieme Verlag Stuttgart · New York

Iridium-Catalyzed Site-Selective C–H Borylation of 2-Pyridones

Wataru Miura
Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan   eMail: k_hirano@chem.eng.osaka-u.ac.jp   eMail: miura@chem.eng.osaka-u.ac.jp
,
Koji Hirano*
Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan   eMail: k_hirano@chem.eng.osaka-u.ac.jp   eMail: miura@chem.eng.osaka-u.ac.jp
,
Masahiro Miura*
Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan   eMail: k_hirano@chem.eng.osaka-u.ac.jp   eMail: miura@chem.eng.osaka-u.ac.jp
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Publikationsverlauf

Received: 24. Januar 2017

Accepted after revision: 07. Februar 2017

Publikationsdatum:
02. März 2017 (online)


Published as part of the Special Topic Modern Strategies for Borylation in Synthesis

Abstract

An iridium-catalyzed site-selective C–H borylation of 2-pyridones has been developed. The site selectivity is predominantly controlled by steric factors, and we can access C4, C5, and C6 C–H on the 2-pyridone ring by the judicious choice of ligand and solvent. Subsequent Suzuki–Miyaura cross-coupling of the borylated products also proceeds to form the corresponding arylated pyridones in good overall yields.

Supporting Information

 
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