The first palladium-catalyzed C-O bond formation method for the synthesis of silacarboxylates by silacarboxylic acids with a broad range of aryl iodides and iodo-N-heterocycles is reported. Electron-deficient, electron-rich, and sterically hindered aryl iodides were well-tolerated to furnish the corresponding aryl silacarboxylates in moderate to excellent yields. Active functional groups, such as -NH, -CHO, and allyl-, showed good tolerance, even in the large-scale synthesis. Double and triple esterification were also demonstrated to be effective.

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http://dx.doi.org/10.1021/acs.orglett.8b02464DOI Listing

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