Synthesis and Solid-State Structure of Substituted Arylphosphine Oxides

Whitaker, Craig; Kott, Kevin L.; McMahon, Robert J.

doi:10.1021/jo00116a042

Cited by 46 publications

(20 citation statements)

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“…The bis(amide) (I) was prepared according to the literature method of Denmark et al (1994) from commercially available (1R,2R)-1,2cyclohexanediamine and tri¯ic anhydride. In the presence of KH in tetrahydrofuran (THF), the bis(amide) yields the dipotassium salt, (II), which, on treatment with diethyl phosphoramidous dichloride (Whitaker et al, 1995), provides phosphine (IIIa) (92% yield; m.p. 336±338 K).…”

Section: Methodsmentioning

confidence: 99%

New electron-deficient chiral phosphines: (4R,5R)-1,3-bis(trifluoromethanesulfonyl)perhydro-1,3,2-benzodiazaphosphol-2-yl] substituted amines

et al. 2002

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Three chiral electron-deficient phosphine ligands, [(4R,15R)-,3-bis(trifluoromethanesulfonyl)perhydro-1,3,2-benzodiazaphosphol-2-yl]diethylamine, C(12)H(20)F(6)N(3)O(4)PS(2), (IIIa), [(4R,5R)-1,3-bis(trifluoromethanesulfonyl)perhydro-1,3,2-benzodiazaphosphol-2-yl]dimethylamine, C(10)H(16)F(6)N(3)O(4)PS(2), (IIIb), and bis[(4R,5R)-1,3-bis(trifluoromethanesulfonyl)perhydro-1,3,2-benzodiazaphosphol-2-yl]methylamine, (IV), as the chloroform solvate, C(17)H(23)F(12)N(5)O(8)P(2)S(4).0.98CHCl(3), have been prepared from (1R,2R)-N,N'-bis(trifluoromethanesulfonyl)-1,2-cyclohexanediamine and diethyl phosphoramidous dichloride, dimethyl phosphoramidous dichloride or methyl imidodiphosphorus tetrachloride. The pi-acceptor abilities of these new types of ligands have been evaluated by X-ray determination of the P-N bond lengths; it has been found that the most promising ligand is the bis(phosphine) (IV).

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Section: Methodsmentioning

confidence: 99%

New electron-deficient chiral phosphines: (4R,5R)-1,3-bis(trifluoromethanesulfonyl)perhydro-1,3,2-benzodiazaphosphol-2-yl] substituted amines

et al. 2002

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“…PCl 2 NEt 2 was prepared according to literature reports. [16] The Merrifield resin was purchased from Polymer Laboratories (PL-CMS Resin, 0.86 mmol g À1 , 75-150 mm). The reaction mixtures were filtered on a Schleicher & Schuell polytetrafluoroethylene membrane filter (0.2 mm).…”

Section: Experimental Section General Remarksmentioning

confidence: 99%

“…The syntheses of 1c-g and 1i and j using this method were in most instances either unsuccessful or tedious despite optimization attempts. By reacting aryllithium reagents with PCl 2 NEt 2 followed by acidification of the reaction mixture with anhydrous HCl [16] (Scheme 1, procedure B), diarylchlorophosphines 1c-g, and 1i and j were obtained with over 90 % purity (determined by 1 H and 31 P NMR of the crude mixtures). Interestingly, the reaction of arylmagnesium bromides with PCl 2 NEt 2 failed and only degradation products could be observed.…”

Section: Introductionmentioning

confidence: 99%

Development of Efficient and Reusable Diarylphosphinopolystyrene‐Supported Palladium Catalysts for CC Bond Forming Cross‐Coupling Reactions

2007

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3c is the most active catalyst for Heck reactions. The couplings are performed under non-anhydrous reaction conditions and require only low amounts of supported palladium (0.5 mequivs. for Suzuki-Miyaura, 1.0 mequiv. for Sonogashira and 0.5 mequivs. for Heck reactions could be sufficient). Catalysts 3a-j are recovered by filtration and can be reused more than four times with no loss of efficiency.

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“…Compound (I) was made as part of a larger synthetic investigation into complexes containing substituted phosphines. The structure of (I) has not previously been reported, although the structure of its corresponding oxide has been described (Whitaker et al, 1995).…”

Section: Commentmentioning

confidence: 99%