Addition of heteroaromatics to alkylidenecyclopropanes catalyzed by palladium

Itaru Nakamura, Amal I. Siriwardana, Shinichi Saito, Yoshinori Yamamoto

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55 Citations (Scopus)

Abstract

The reaction of heteroaromatics, such as furans, thiophenes, thiazoles, and pyrroles, with alkylidenecyclopropanes proceeded smoothly in the presence of palladium catalysts, producing the corresponding α-allylated products in good to high yields. For example, the reaction of 3-butylpentylidenecyclopropane (1a) with 2-methylfuran (2a), ethyl 2-thiophenecarboxylate (4a), 2-isobutylthiazole (6a), and 1-methylpyrrole (11b) gave the α-allylated products in 70%, 66%, 77%, and 30% yield, respectively. The reaction proceeded predominantly through distal bond cleavage. The order of reactivity of heteroaromatics toward 1a is as follows: furan > thiophene ≈ thiazole (5-position) > thiazole (2-position) ≈ pyrrole. This methodology provides a means for introducing an allylic group to various kinds of heteroaromatics under mild conditions.

Original languageEnglish
Pages (from-to)3445-3449
Number of pages5
JournalJournal of Organic Chemistry
Volume67
Issue number10
DOIs
Publication statusPublished - 2002 May 17

ASJC Scopus subject areas

  • Organic Chemistry

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