Triphenylphosphine

Cobb, Jeff E.; Cribbs, Cynthia M.; Henke, Brad R.; Uehling, David; Hernan, Alejandro G.; Martin, Colin; Rayner, Christopher M.

doi:10.1002/047084289x.rt366

“…1 In transformations that employ triphenylphosphine (TPP) as a reductant, the triphenylphosphine is converted to triphenylphosphine oxide (TPPO). Although in some cases separation of TPPO from the reaction product is easily achieved, the difficulty of the separation is often cited as a barrier to using TPP as a reductant or reagent.…”

Section: Introductionmentioning

confidence: 99%

“…1,6 Separation by distillation is useful for cases where the reaction product is sufficiently stable and low-boiling, 7 but a liquid–liquid or liquid–solid phase separation would be more generally useful. TPPO can be precipitated in cases where the reaction product is soluble in very nonpolar solvents, such as cold hexanes and diethyl ether mixtures.…”

Section: Introductionmentioning

confidence: 99%

Removal of Triphenylphosphine Oxide by Precipitation with Zinc Chloride in Polar Solvents

Batesky

¹

,

Goldfogel

²

,

Weix

³

2017

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While the use of triphenylphosphine as a reductant is common in organic synthesis, the resulting triphenylphosphine oxide (TPPO) waste can be difficult to separate from the reaction product. While a number of strategies to precipitate TPPO are available, none have been reported to work in more polar solvents. We report here that mixing ZnCl2 with TPPO precipitates a TPPO–Zn complex in high yield in several common polar organic solvents. The solvent compatibility of this procedure and the reliability of the precipitation in the presence of polar functional groups were examined to show the utility and limitations of this method.

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“…Reduction of the ester group of the furan 3b produced an alcohol intermediate, [32] which we transformed to ah alide.S urprisingly,t he bromide was unstable, [33] but the iodide proved to be robust and was converted smoothly to the phosphonium iodide 4 when using PPh 3 as the reaction solvent. [34] Asubsequent Wittig reaction under Bodensc onditions [35] furnished rosefuran in 97 % yield. To prevent complications resulting from lithiation of the free C5 position of 4,w ec hose KOtBu as the base.W e used the same approach for the syntheses of sesquirosefuran [36] and mikanifuran.…”

Section: Resultsmentioning

confidence: 99%

Unified Approach to Furan Natural Products via Phosphine‐Palladium Catalysis

Chen

¹

,

Kwon

²

2021

Angewandte Chemie

5

0

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Polyalkyl furans are widespread in nature,o ften performing important biological roles.D espite ap lethora of methods for the synthesis of tetrasubstituted furans,t he construction of tetraalkylf urans remains non-trivial. The prevalence of alkylgroups in bioactive furan natural products, combined with the desirable bioactivities of tetraalkylf urans, calls for ageneral synthetic protocol for polyalkylfurans.This paper describes aM ichael-Heck approach, using sequential phosphine-palladium catalysis,f or the preparation of various polyalkylf urans from readily available precursors.T he versatility of this method is illustrated by the total syntheses of nine distinct polyalkylated furan natural products belonging to different classes,n amely the furanoterpenes rosefuran, sesquirosefuran, and mikanifuran;the marine natural products plakorsins A, B, and Dand plakorsin Dmethyl ester;and the furan fatty acids 3D5 and hydromumiamicin.

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Unified Approach to Furan Natural Products via Phosphine‐Palladium Catalysis

Chen

¹

,

Kwon

²

2021

View full text Add to dashboard Cite

Polyalkyl furans are widespread in nature,o ften performing important biological roles.D espite ap lethora of methods for the synthesis of tetrasubstituted furans,t he construction of tetraalkylf urans remains non-trivial. The prevalence of alkylgroups in bioactive furan natural products, combined with the desirable bioactivities of tetraalkylf urans, calls for ageneral synthetic protocol for polyalkylfurans.This paper describes aM ichael-Heck approach, using sequential phosphine-palladium catalysis,f or the preparation of various polyalkylf urans from readily available precursors.T he versatility of this method is illustrated by the total syntheses of nine distinct polyalkylated furan natural products belonging to different classes,n amely the furanoterpenes rosefuran, sesquirosefuran, and mikanifuran;the marine natural products plakorsins A, B, and Dand plakorsin Dmethyl ester;and the furan fatty acids 3D5 and hydromumiamicin.

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Triphenylphosphine

Abstract: TriphenylphosphinePh 3 P [603-35-0] C 18 H 15 P (MW 262.30) InChI = 1/C18H15P/c1-

Cited by 3 publications

References 98 publications

Removal of Triphenylphosphine Oxide by Precipitation with Zinc Chloride in Polar Solvents

Removal of Triphenylphosphine Oxide by Precipitation with Zinc Chloride in Polar Solvents

Unified Approach to Furan Natural Products via Phosphine‐Palladium Catalysis

Unified Approach to Furan Natural Products via Phosphine‐Palladium Catalysis

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