As we know that the ester is one of the most important functional groups in chemicals[1]. Among various types of esters, methyl one is frequently appeared as building blocks in various natural products and polymers[2,...
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As we know that the ester is one of the most important functional groups in chemicals[1]. Among various types of esters, methyl one is frequently appeared as building blocks in various natural products and polymers[2,3]. In this report, we have successfully developed a highly effective synthesis of methyl esters from benzylic alcohols, aldehydes or acids for the first time via copper-catalyzed C-C cleavage from tert-butyl hydroperoxide. It is noteworthy that in this transformation, TBHP plays the role of both the oxidant and the source of methyl group. In addition, our system not only can be used in the methyl esterification of alcohol, aldehyde and acid, but also provide a protection method of N-methylation. Our protocol was easily accessible and practical, which will be the possible supplement for the traditional way.
Ketene dithioacetals(Figure 1) are versatile intermediates in organic synthesis[1-4]. Based on the structural features, the α-carbon of ketene dithioacetals is reactive towards electrophiles(Figure 1)[1,2], and this ...
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Ketene dithioacetals(Figure 1) are versatile intermediates in organic synthesis[1-4]. Based on the structural features, the α-carbon of ketene dithioacetals is reactive towards electrophiles(Figure 1)[1,2], and this electrophilic susceptibility makes the α-functionalization of ketene dithioacetals a convenient tool for the construction of diverse ketene dithioacetal scaffolds and other useful building blocks. For example, the α-trifluoromethylation of ketene dithioacetals can been performed in a single step by the direct sp2C–H trifluoromethylation of a ketene dithioacetal with trifluoromethyltrimethylsilane(TMSCF3) in the presence of Ph I(OAc)2 as an oxidant(Scheme 1)[5]. In addition, the reactions of ketene dithioacetals tuned by alkylthio functionality have been found useful in a broad range that allows for more flexibility in synthetic design. Thus, the α-functionalization of ketene dithioacetals provides an effective means for ongoing research activities related.
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