Synthesis 2007(3): 464-477  
DOI: 10.1055/s-2006-958949
FEATUREARTICLE
© Georg Thieme Verlag Stuttgart · New York

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;
Further Information

Publication History

Received 2 August 2006
Publication Date:
14 December 2006 (online)

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.

31

Compounds 33 were used without further purification.

33

Analytical data of 23a and 24j are given in Table [5] . For 23b and 24k, see ref. 34. For 24a-i, see ref. 18a.

38

Compounds 66 and 67 are commercially available.