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Synthesis 2009(7): 1075-1080
DOI: 10.1055/s-0028-1083356
DOI: 10.1055/s-0028-1083356
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
One-Pot Synthesis of 1,4-Diarylnaphthalenes via a Wittig-Horner Reaction/[4+2] Cycloaddition/Dehydrogenation Sequence
Further Information
Publication History
Received
14 October 2008
Publication Date:
11 February 2009 (online)


Abstract
A one-pot synthesis of 1,4-diarylnaphthalenes from cinnamaldehydes, dimethyl benzylphosphonates, and benzenediazonium-2-carboxylate is described. The tandem process involves the Wittig-Horner reaction of the cinnamaldehyde with the benzylphosphonate, [4+2] cycloaddition of the thus-formed diene with benzyne, and subsequent dehydrogenation. The procedure is general and efficient and the substrates are readily available.
Key words
diphenylnaphthalene - tandem reaction - Wittig-Horner reaction - cycloaddition - benzyne