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Synlett 2003(13): 2057-2061  
DOI: 10.1055/s-2003-42049
LETTER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 2-(Diarylmethylene)-3-benzofuranones Promoted via Palladium-Catalyzed Reactions of Aryl iodides with 3-Aryl-1-(2- tert-butyldimethyl­silyloxy)phenyl-2-propyn-1-ones

Chi-Fong Lin, Wen-Der Lu, I-Wen Wang, Ming-Jung Wu*
School of Chemistry, Kaohsiung Medical University, Kaohsiung, Taiwan
Fax: +886(7)3125339; e-Mail: mijuwu@cc.kmu.edu.tw;
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Publication History

Received 25 July 2003
Publication Date:
08 October 2003 (online)

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Abstract

3-Substituted-1-(2-tert-butyldimethylsilyloxy)phenyl-2-propyn-1-ones were coupled with aryl iodides by using palladium as a catalyst in ambient MeOH solution and gave 2-(diarylmethylene)-3-benzofuranones in moderate to good yields.

Key words

palladium - coupling - cyclizations

7

Treatment of 2-hydroxybenzaldehyde with TBDMSCl and imidazole gave compound 6 in 95% yield. Applying phenylacetylene with n-BuLi in THF resulted a respective lithium salt. Subsequent exposure the aldehyde 6 to the lithium salt provided the alcohol 7a in 90% yield. The α,β-unsaturated ketone 1a was obtained by oxidation of 7a with MnO2 in 90% yield.