Synthesis of olefins via a Wittig reaction mediated by triphenylarsine

Li, Lun; Stimac, Jared C.; Geary, Laina M.

doi:10.1016/j.tetlet.2017.02.051

“…[ E -Isomer (CAS no. 29246-70-6)]: 1 H NMR (400 MHz, CDCl 3 ) δ 8.28 (d, J = 8.7 Hz, 2H), 7.64 (d, J = 8.7 Hz, 2H), 7.47 (d, J = 16.5 Hz, 1H), 6.06 (d, J = 16.5 Hz, 1H); 13 C{ 1 H} NMR (100 MHz, CDCl 3 ) δ 149.2, 147.8, 139.3, 128.2, 124.5, 117.1, 101.1.…”

Section: Methodsmentioning

confidence: 99%

Phosphorus-Recycling Wittig Reaction: Design and Facile Synthesis of a Fluorous Phosphine and Its Reusable Process in the Wittig Reaction

Yamamoto

¹

,

Kawaguchi

²

,

Nishimura

³

et al. 2020

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This study shows that phosphorus sources can be recycled using the appropriate fluorous phosphine in the Wittig reaction. The designed fluorous phosphine, which has an ethylene spacer between its phosphorus atom and the perfluoroalkyl group, was synthesized from air-stable phosphine reagents. The synthesized phosphine can be used for the Wittig reaction process to obtain various alkenes in adequate yields and stereoselectivity. The concomitantly formed fluorous phosphine oxide was extracted from the reaction mixture using a fluorous biphasic system. The fluorous phosphine was regenerated by reducing the fluorous phosphine oxide with diisobutylaluminum hydride. Finally, a series of gram scale phosphorus recycling processes were performed, which included the Wittig reaction, separation, reduction, and reuse.

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“…[42] We hoped that the increased reactivity of the Ph 3 As = O might make its reduction compatible with an anodic cyclization in the presence of the required methanol solvent and thereby provide information on the reduction potential needed for such a process. This alternative for Ph 3 P=O was intriguing because Geary and co-workers have demonstrated that Wittig reactions can be conducted with the use of Ph 3 As in place of the Ph 3 P. [43,44] The reduction of Ph 3 As=O was initially paired with the oxidation of veratryl alcohol [Scheme 10, Eq. (a)].…”

Section: Pairing Oxidations With the Reduction Of Ph 3 P = Omentioning

confidence: 99%

Organic Electrochemistry: Expanding the Scope of Paired Reactions

Wu

¹

,

Moeller

²

2021

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Paired electrochemical reactions allow the optimization of both atom and energy economy of oxidation and reduction reactions. While many paired electrochemical reactions take advantage of perfectly matched reactions at the anode and cathode, this matching of substrates is not necessary. In constant current electrolysis, the potential at both electrodes adjusts to the substrates in solution. In principle, any oxidation reaction can be paired with any reduction reaction. Various oxidation reactions conducted on the anodic side of the electrolysis were paired with the generation and use of hydrogen gas at the cathode, showing the generality of the anodic process in a paired electrolysis and how the auxiliary reaction required for the oxidation could be used to generate a substrate for a non-electrolysis reaction. This is combined with variations on the cathodic side of the electrolysis to complete the picture and illustrate how oxidation and reduction reactions can be combined.

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“…We hoped that the increased reactivity of the Ph 3 As=O might make its reduction compatible with an anodic cyclization in the presence of the required methanol solvent and thereby provide information on the reduction potential needed for such a process. This alternative for Ph 3 P=O was intriguing because Geary and co‐workers have demonstrated that Wittig reactions can be conducted with the use of Ph 3 As in place of the Ph 3 P [43, 44] …”

Section: Introductionmentioning

confidence: 99%

Organic Electrochemistry: Expanding the Scope of Paired Reactions

Wu

¹

,

Moeller

²

2021

View full text Add to dashboard Cite

Paired electrochemical reactions allow the optimization of both atom and energy economy of oxidation and reduction reactions. While many paired electrochemical reactions take advantage of perfectly matched reactions at the anode and cathode, this matching of substrates is not necessary. In constant current electrolysis, the potential at both electrodes adjusts to the substrates in solution. In principle, any oxidation reaction can be paired with any reduction reaction. Various oxidation reactions conducted on the anodic side of the electrolysis were paired with the generation and use of hydrogen gas at the cathode, showing the generality of the anodic process in a paired electrolysis and how the auxiliary reaction required for the oxidation could be used to generate a substrate for a non-electrolysis reaction. This is combined with variations on the cathodic side of the electrolysis to complete the picture and illustrate how oxidation and reduction reactions can be combined.

show abstract

Synthesis of olefins via a Wittig reaction mediated by triphenylarsine

Cited by 12 publications

References 35 publications

Phosphorus-Recycling Wittig Reaction: Design and Facile Synthesis of a Fluorous Phosphine and Its Reusable Process in the Wittig Reaction

Phosphorus-Recycling Wittig Reaction: Design and Facile Synthesis of a Fluorous Phosphine and Its Reusable Process in the Wittig Reaction

Organic Electrochemistry: Expanding the Scope of Paired Reactions

Organic Electrochemistry: Expanding the Scope of Paired Reactions

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