Borylation using group IV metallocene under mild conditions

•We developed a borylation reaction of diazonium salts.•Di(isopropyl)aminoborane is used as borylation agent.•Mechanism is thought to proceed through a radical pathway.•Zr- and Ti-centered metallocenes were the most efficient initiators.•Many boronates were obtained including with halide substitutio...

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Bibliographic Details
Published inTetrahedron letters Vol. 55; no. 10; pp. 1702 - 1705
Main Authors Marciasini, Ludovic D., Vaultier, Michel, Pucheault, Mathieu
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 05.03.2014
Elsevier
Subjects
Boron
Catalysis
Chemistry
Chemistry, Organic
Derivatives
Metallocene
Metallocenes
Pathways
Physical Sciences
Radical
Radicals
Reaction mechanisms
Science & Technology
Tetrahedrons
Titanium
Transesterification
Zirconium
Titanium
Boron
Zirconium
Metallocene
Radical
HALIDES
CROSS-COUPLING REACTION
MECHANISM
COMPLEXES
NANOCRYSTALS
SALTS
FUNCTIONALIZATION
PALLADIUM-CATALYZED BORYLATION
TRANSITION-METAL
CHEMISTRY
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Summary:•We developed a borylation reaction of diazonium salts.•Di(isopropyl)aminoborane is used as borylation agent.•Mechanism is thought to proceed through a radical pathway.•Zr- and Ti-centered metallocenes were the most efficient initiators.•Many boronates were obtained including with halide substitution. A borylation reaction of aromatic diazonium salts has been optimized using titanocene and zirconocene derivatives as catalysts. The reaction employs diisopropylaminoborane as a borylating agent and proceeds smoothly at room temperature to provide arylboronates after methanolysis and transesterification with pinacol. The reaction mechanism has been found to proceed via a radical pathway.
Bibliography:ObjectType-Article-1
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ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2014.01.080