Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Palladium-Catalyzed 1-Methylene-2-propenylation Reactions of Aryl Bromides with 3,4-Alkadien-1-ols via Carbon–Carbon Bond Cleavage for the Synthesis of 2-Aryl-1,3-butadiene Derivatives
Junichi ImotoSayuri HayashiKoji HiranoHideki YorimitsuKoichiro Oshima
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2009 Volume 82 Issue 3 Pages 393-400

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Abstract

A method for the synthesis of 2-aryl-1,3-alkadienes has been developed. Treatment of aryl bromides with 3,4-alkadien-1-ols in the presence of a palladium catalyst results in 1-methylene-2-propenyl group transfer to aryl bromides. Taking advantage of palladium-mediated retro-allylation as an sp3C–sp3C bond cleavage reaction, one can regard 3,4-alkadien-1-ols as 1-methylene-2-propenyl metal equivalents that are easy to prepare and are not sensitive to air and moisture. In the event that the Diels–Alder dimerization of the product during the 1-methylene-2-propenylation reaction is problematic, addition of N-methylpyrrole to the reaction mixture can efficiently suppress the dimerization. The reactions of aryl bromides with 2-substituted 3,4-alkadien-1-ols yield the corresponding (E)-2-aryl-1,3-alkadienes stereoselectively.

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© 2009 The Chemical Society of Japan
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