C–H Borylation by Platinum Catalysis

Herein, we describe the platinum-catalyzed borylation of aromatic C–H bonds. N-Heterocyclic carbene-ligated platinum catalysts are found to be efficient catalysts for the borylation of aromatic C(sp2)–H bonds when bis(pinacolato)diboron is used as the boron source. The most remarkable feature of the...

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Bibliographic Details
Published inBulletin of the Chemical Society of Japan Vol. 90; no. 3; pp. 332 - 342
Main Authors Furukawa, Takayuki, Tobisu, Mamoru, Chatani, Naoto
Format Journal Article
LanguageEnglish
Published TOKYO The Chemical Society of Japan 15.03.2017
Chemical Soc Japan
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
DIRECTING GROUP
TRANSITION-METAL CATALYSIS
N-HETEROCYCLIC CARBENE
CARBON-OXYGEN BONDS
REDUCTIVE ELIMINATION PROCESSES
IRIDIUM CATALYST
RUTHENIUM COMPLEXES
REGIOSPECIFIC FUNCTIONALIZATION
HYDROSILYLATION CATALYSTS
GRIGNARD-REAGENTS
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Summary:Herein, we describe the platinum-catalyzed borylation of aromatic C–H bonds. N-Heterocyclic carbene-ligated platinum catalysts are found to be efficient catalysts for the borylation of aromatic C(sp2)–H bonds when bis(pinacolato)diboron is used as the boron source. The most remarkable feature of these Pt catalysts is their lack of sensitivity towards the degree of steric hindrance around the C–H bonds undergoing the borylation reaction. These Pt catalysts allow for the synthesis of sterically congested 2,6-disubstituted phenylboronic esters, which are otherwise difficult to synthesize using existing C–H borylation methods. Furthermore, platinum catalysis allows for the site-selective borylation of the C–H bonds ortho to fluorine substituents in fluoroarene systems. Preliminary mechanistic studies and work towards the synthetic application of this platinum catalyzed C–H borylation process are described.
Bibliography:KAKEN
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.20160391