Palladium-Promoted Intramolecular Addition of an Aryl Iodide to a Nitroalkene

Scott E. Denmark; Mark E. Schnute

doi:10.1021/jo00109a037

Palladium-Promoted Intramolecular Addition of an Aryl Iodide to a Nitroalkene

Scott E. Denmark, Mark E. Schnute

Chemistry

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Abstract

Iodoaryl nitroalkene 9 was found to undergo a palladium-promoted Heck cyclization in the presence of Pd (OAc)₂ (1.0 equiv), triphenylphosphine (2.0 equiv), and Ag₂CO₃ (2.0 equiv) in benzene at 25 °C to afford exocyclic 2, 2-disubstituted-l-nitroalkene (Z)-2 as a single geometrical isomer (43%) along with the corresponding saturated nitroalkane 10 (40%). Subsequent selenylation of the nitroalkane, oxidative elimination, and olefin isomerization afforded (Z)-2 in 70% yield. The influence of Ag₂CO₃ and solvent on the cyclization and the mechanism of nitroalkane formation are proposed.

Original language	English (US)
Pages (from-to)	1013-1019
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	60
Issue number	4
DOIs	https://doi.org/10.1021/jo00109a037
State	Published - Feb 1 1995

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Organic Chemistry

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abstract = "Iodoaryl nitroalkene 9 was found to undergo a palladium-promoted Heck cyclization in the presence of Pd (OAc)2 (1.0 equiv), triphenylphosphine (2.0 equiv), and Ag2CO3 (2.0 equiv) in benzene at 25 °C to afford exocyclic 2, 2-disubstituted-l-nitroalkene (Z)-2 as a single geometrical isomer (43%) along with the corresponding saturated nitroalkane 10 (40%). Subsequent selenylation of the nitroalkane, oxidative elimination, and olefin isomerization afforded (Z)-2 in 70% yield. The influence of Ag2CO3 and solvent on the cyclization and the mechanism of nitroalkane formation are proposed.",

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N2 - Iodoaryl nitroalkene 9 was found to undergo a palladium-promoted Heck cyclization in the presence of Pd (OAc)2 (1.0 equiv), triphenylphosphine (2.0 equiv), and Ag2CO3 (2.0 equiv) in benzene at 25 °C to afford exocyclic 2, 2-disubstituted-l-nitroalkene (Z)-2 as a single geometrical isomer (43%) along with the corresponding saturated nitroalkane 10 (40%). Subsequent selenylation of the nitroalkane, oxidative elimination, and olefin isomerization afforded (Z)-2 in 70% yield. The influence of Ag2CO3 and solvent on the cyclization and the mechanism of nitroalkane formation are proposed.

AB - Iodoaryl nitroalkene 9 was found to undergo a palladium-promoted Heck cyclization in the presence of Pd (OAc)2 (1.0 equiv), triphenylphosphine (2.0 equiv), and Ag2CO3 (2.0 equiv) in benzene at 25 °C to afford exocyclic 2, 2-disubstituted-l-nitroalkene (Z)-2 as a single geometrical isomer (43%) along with the corresponding saturated nitroalkane 10 (40%). Subsequent selenylation of the nitroalkane, oxidative elimination, and olefin isomerization afforded (Z)-2 in 70% yield. The influence of Ag2CO3 and solvent on the cyclization and the mechanism of nitroalkane formation are proposed.

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Palladium-Promoted Intramolecular Addition of an Aryl Iodide to a Nitroalkene

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