A New Performance of the Reaction of PCl3/AlCl3 with Anisoles − One-Pot and Multi-Step Syntheses of a New Fused-Ring System [1,2,3]Benzoxadiphospholo[2,3-b][1,2,3]benzoxadiphosphole

Baccolini, Graziano; Bazzocchi, Marco Antonio; Boga, Carla

doi:10.1002/1099-0690(200106)2001:12<2229::aid-ejoc2229>3.0.co;2-t

Cited by 7 publications

(3 citation statements)

References 14 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Flash column chromatography was carried out using 35-75 µm particle size silica gel. Secondary diarylphosphine oxides 1a, 17 1b, 20 1c, 16 1d 21 and 1e, 22 and cyclic sulfamidates 2a, 2b and 2c, 15 were synthesized according to published protocols.…”

Section: General Methodsmentioning

confidence: 99%

A versatile synthesis of chiral β-aminophosphines

Song

Taylor

2016

Org. Biomol. Chem.

View full text Add to dashboard Cite

A method for the preparation of chiral β-aminophosphines having substituted P-aryl groups is described. Ring-opening of cyclic sulfamidates with metal diarylphosphinites yields β-aminophosphine oxides, which are then reduced to the corresponding phosphines. Effects of the diarylphosphinite countercation on the regioselectivity of the ring-opening reaction (P- versus O-alkylation) are discussed. This method enables the introduction of electron-deficient, electron-rich and sterically hindered diarylphosphino groups, as demonstrated by the synthesis of a series of novel, P-aryl-substituted β-aminophosphines derived from tert-leucinol, valinol and phenylglycinol. Access to these derivatives will create new opportunities for steric and electronic tuning of β-aminophosphine-derived chiral ligands and organocatalysts.

show abstract

Section: General Methodsmentioning

confidence: 99%

A versatile synthesis of chiral β-aminophosphines

Song

Taylor

2016

Org. Biomol. Chem.

View full text Add to dashboard Cite

show abstract

“…Phosphophosphidites, (R′O) 2 P–PR 2 are examples of heterodiphosphanes but their chemistry has been little studied . They are the phosphorus congeners of the well‐known phosphoramidites (R′O) 2 P–NR 2 which have found important applications in a variety of homogeneous metal‐catalysed asymmetric reactions, and are used extensively as intermediates in oligonucleotide synthesis .…”

Section: Introductionmentioning

confidence: 99%

Phosphophosphidites Derived from BINOL

et al. 2019

View full text Add to dashboard Cite

Phosphophosphidites of the type R 2 P-P(binol) [where binol = the dianion of (S)-1,1′-bi-2-naphthol] are the phosphorus analogues of the ubiquitous phosphoramidites, R 2 N-P(binol) and are readily accessed by the chlorosilane elimination reaction between R 2 P-SiMe 3 and Cl-P(binol). The crystal structure of iPr 2 P-P(binol) (1) has been determined and shows a P-P bond length in the normal range. The solution reactions of 1 have been investigated, principally by 31 P NMR spectro- IntroductionHomodiphosphanes Z 2 P-PZ 2 are amongst the simplest catenated phosphorus species and are known with a wide variety Scheme 1. Illustration of the array of reactions undergone by Ph 2 P-PPh 2 involving (a) P-P bond cleavage or (b) P-P bond retention.[a] Synthesis of Bis(borane) Adduct 13: A solution of H 3 B·SMe 2 (7.0 mg, 0.092 mmol) in CH 2 Cl 2 (0.3 mL) was added to a solution of 1 (20 mg, 0.046 mmol) in CH 2 Cl 2 (0.3 mL) and transferred to a J Young NMR tube. The solution was kept at ambient temperature for 30 min and then the volatiles were removed under reduced pressure to give a white solid, (20 mg, 94 %). 31 P{ 1 H} NMR (CD 2 Cl 2 , 162 MHz) (δ, ppm): 181.8 (br. d, J = 210 Hz), 47.6 (d, J = 210 Hz). 11 B{ 1 H} NMR (CD 2 Cl 2 , 128 MHz) (δ, ppm): -38.9 (br. s, 1B), -44.1 (br. s, 1B). 1 H NMR (CD 2 Cl 2 , 400 MHz) (δ, ppm): 8.07 (dd, 2H, J = 17.8 Hz, 9.0 Hz, Ar-CH), 8.00 (t, 2H, J = 7.7 Hz, Ar-CH), 7.64 (dd, 1H, J = 8.9 Hz, 1.0 Hz, ArCH), 7.51 (m, 3H, ArCH), 7.28 (m, 3H, ArCH), 7.18 (d, 1H, J = 8.6 Hz, Ar-CH), 2.72 (ddsept, 1H, J = 14.3 Hz, 11.0 Hz, 7.2 Hz, iPr-CH), 2.72 (dtt, 1 H, J = 14.3 Hz, 9.5 Hz, 7.2 Hz, iPr -CH), 1.4 (dd, 3H, J = 15.5 Hz, 7.1 Hz, iPr -CH 3 ), 1.40 (dd, 3H, J = 16.2 Hz, 7.1 Hz, iPr Eur.

show abstract

“…Phosphophosphidites, (R'O) 2 P-PR 2 are examples of heterodiphosphanes but their chemistry has been little studied. 18,19,20 They are the phosphorus congeners of the well-known phosphoramidites (R'O) 2 P-NR 2 which have found important applications in a variety of homogeneous metal-catalysed asymmetric reactions 21,22 and are used extensively as intermediates in oligonucleotide synthesis. 23 Here we report the synthesis and properties of the optically active 1,1'-bi-2-naphthol-derived phosphophosphidite 1 and related species and draw comparisons with the phosphoramidite analogue A.…”

Section: Introductionmentioning

confidence: 99%