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In the absence of manganese(IV) oxide, the combination of aldehydes with triazolium salt E and DBU yielded only benzoin products. See: (a) Breslow, R, Schmuck, C. Tetrahedron Lett. 1996, 37, 8241-8242
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Acyl heteroazolium species have been proposed as acylating agents in several NHC-catalyzed processes. See: (a) Suzuki, Y.; Yamauchi, K.; Muramatsu, K.; Sato, M. Chem. Commun. 2004, 2770-2771.
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In a related, but strongly discouraging result, Taylor reported that 2 full equiv of a thiazolium salt in the presence of 20 equiv of manganese(IV) oxide only afforded 4% yield (calculated by 1H NMR) of methylcinnamate from cinnamyl alcohol see ref 5
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1H NMR) of methylcinnamate from cinnamyl alcohol (see ref 5).
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The use of cis-allylic alcohols in this reaction leads to slower reaction times and partial isomerization of the double bond (1:5 E/Z mixture). n-Butyl cis-cinnamate can be isolated in moderate yield (62%).
-
The use of cis-allylic alcohols in this reaction leads to slower reaction times and partial isomerization of the double bond (1:5 E/Z mixture). n-Butyl cis-cinnamate can be isolated in moderate yield (62%).
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See Supporting Information for details.
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