Arylboronic acids as versatile coupling partners in fast microwave promoted oxidative Heck chemistry

The useful and selective reactivity of arylboronic acids makes them favourite building blocks for many modern organic chemistry applications like the metal-mediated formation of C-C, C-O, C-N, and C-S bonds. This report describes oxidative Heck coupling reactions of arylboronic acids and olefins, wh...

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Bibliographic Details
Published in:Molecular diversity 2003, Vol.7 (2-4), p.97-106
Main Authors: Andappan, Murugaiah M S, Nilsson, Peter, Larhed, Mats
Format: Article
Language:English
Subjects:
Acids
Alkenes - chemistry
Boronic Acids - chemistry
Catalysis
Chemistry
Chemistry, Organic - methods
Hot Temperature
Hydrocarbons, Aromatic - chemistry
Microwave heating
Microwaves
Models, Chemical
Oxygen - metabolism
Solvents
Temperature
Time Factors
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Summary:The useful and selective reactivity of arylboronic acids makes them favourite building blocks for many modern organic chemistry applications like the metal-mediated formation of C-C, C-O, C-N, and C-S bonds. This report describes oxidative Heck coupling reactions of arylboronic acids and olefins, which were conveniently and rapidly (5-30 min) carried out under air with temperature-controlled microwave heating. Different reaction conditions were investigated with regard to both microwave heating capability and chemical productivity. Copper(II) acetate was identified as a microwave compatible reoxidant of Pd(0). The scope and limitations of this high-speed chemistry protocol with diverse olefins and organoboronic acids are discussed.
ISSN:1381-1991
1573-501X
1573-501X
DOI:10.1023/B:MODI.0000006803.99656.8c