The Photo-Dehydro-Diels-Alder (PDDA) Reaction - A Powerful Method for the Preparation of Biaryls

Pablo Wessig; Gunnar Müller; Charlotte Pick; Annika Matthes

doi:10.1055/s-2006-958949

FEATUREARTICLE

The Photo-Dehydro-Diels-Alder (PDDA) Reaction - A Powerful Method for the Preparation of Biaryls

Pablo Wessig*, Gunnar Müller, Charlotte Pick, Annika Matthes
Institut für Chemie, Humboldt-Universität zu Berlin, Brook-Taylor-Str. 2, 12489 Berlin, Germany
Fax: +49(30)20937450; e-Mail: pablo.wessig@chemie.hu-berlin.de;

Abstract

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Abstract

The photochemically initiated dehydro-Diels-Alder (PDDA) reaction is an efficient and versatile method for the preparation of biaryls. The ring closure may take place both inter- and intramolecularly, of which the intramolecular variant is more productive from the preparative point of view. A variety of linkers can be employed to connect the ynone moiety, which acts as the chromophore, with another acetylene group, thus allowing large structural versatility. Principles influencing the site selectivity of the PDDA reaction will also be discussed here.

Key words

photochemistry - biaryls - alkynes - photo-dehydro-Diels-Alder reaction - cyclizations

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References

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