Palladium-Catalyzed C-CN activation for intramolecular cyanoesterification of alkynes

Naveen R. Rondla; Samuel M. Levi; Jonathan M. Ryss; Rachel A.Vanden Berg; Christopher J. Douglas

doi:10.1021/ol200274h

Palladium-Catalyzed C-CN activation for intramolecular cyanoesterification of alkynes

Naveen R. Rondla, Samuel M. Levi, Jonathan M. Ryss, Rachel A.Vanden Berg, Christopher J. Douglas

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

43 Scopus citations

Abstract

Conditions for the C-CN activation and intramolecular cyanoesterification of alkynes to provide butenolides in good to excellent yields are presented. Pd catalysts, high temperatures/short reaction times (microwave irradiation), and Lewis basic solvents minimized competitive decarbonylation. Less sterically encumbered, electron-rich alkynes underwent cyanoesterification with greater ease compared to sterically encumbered, electron-deficient alkynes. The results led to the hypothesis that migratory insertion of the alkyne, rather than C-CN activation, might be the product-determining step.

Original language	English (US)
Pages (from-to)	1940-1943
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	8
DOIs	https://doi.org/10.1021/ol200274h
State	Published - Apr 15 2011

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abstract = "Conditions for the C-CN activation and intramolecular cyanoesterification of alkynes to provide butenolides in good to excellent yields are presented. Pd catalysts, high temperatures/short reaction times (microwave irradiation), and Lewis basic solvents minimized competitive decarbonylation. Less sterically encumbered, electron-rich alkynes underwent cyanoesterification with greater ease compared to sterically encumbered, electron-deficient alkynes. The results led to the hypothesis that migratory insertion of the alkyne, rather than C-CN activation, might be the product-determining step.",

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AU - Levi, Samuel M.

AU - Ryss, Jonathan M.

AU - Berg, Rachel A.Vanden

AU - Douglas, Christopher J.

PY - 2011/4/15

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N2 - Conditions for the C-CN activation and intramolecular cyanoesterification of alkynes to provide butenolides in good to excellent yields are presented. Pd catalysts, high temperatures/short reaction times (microwave irradiation), and Lewis basic solvents minimized competitive decarbonylation. Less sterically encumbered, electron-rich alkynes underwent cyanoesterification with greater ease compared to sterically encumbered, electron-deficient alkynes. The results led to the hypothesis that migratory insertion of the alkyne, rather than C-CN activation, might be the product-determining step.

AB - Conditions for the C-CN activation and intramolecular cyanoesterification of alkynes to provide butenolides in good to excellent yields are presented. Pd catalysts, high temperatures/short reaction times (microwave irradiation), and Lewis basic solvents minimized competitive decarbonylation. Less sterically encumbered, electron-rich alkynes underwent cyanoesterification with greater ease compared to sterically encumbered, electron-deficient alkynes. The results led to the hypothesis that migratory insertion of the alkyne, rather than C-CN activation, might be the product-determining step.

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Palladium-Catalyzed C-CN activation for intramolecular cyanoesterification of alkynes

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