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. 2011 Jun 3;13(11):2834-6.
doi: 10.1021/ol200794w. Epub 2011 May 2.

Syntheses of α-pyrones using gold-catalyzed coupling reactions

Tuoping Luo  1 , Mingji Dai, Shao-Liang Zheng, Stuart L Schreiber
Affiliations
Free PMC article

Syntheses of α-pyrones using gold-catalyzed coupling reactions

Tuoping Luo et al. Org Lett. .
Free PMC article

Abstract

Sequential alkyne activation of terminal alkynes and propiolic acids by gold(I) catalysts yields compounds having α-pyrone skeletons. Novel cascade reactions involving propiolic acids are reported that give rise to α-pyrones with different substitution patterns.

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Figures

Figure 1
Figure 1
Syntheses of α-pyrones via gold(I)-catalyzed cascade reactions.
Figure 2
Figure 2
Cyclization of vinyl propiolate 5a into α-pyrone 6a.
Figure 3
Figure 3
Dimerization of propiolic acid leading to 4-hydroxy α-pyrone.
Scheme 1
Scheme 1. Gold(I)-Catalyzed Syntheses of α-Pyrones from Propiolic Acids and Alkynes
Reaction conditions: propiolic acid (0.2–0.7 mmol, 0.2 M), alkyne (5–6 equiv), [(Ph3P)AuCl]/AgOTf (5 mol %), CH2Cl2, rt, 12 h; bphenylpropiolic acid (3.4 mmol), alkyne (5 equiv), [(Ph3P)AuCl]/AgOTf (5 mol %), CH2Cl2, rt, 24 h; cCH2Cl2, 50 °C, 12 h; d3-(naphthalene-2-yl)propiolic acid (0.1 M); ephenylacetylene (6 equiv), toluene, 60 °C, slow addition of acid (over 2 h), 12 h; f2-butyne (10 equiv), toluene, 60 °C, 12 h.
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