Selective catch and release of a synthetically useful phosphine ligand

Tetrahedron Letters

Volumn 44, Issue 40, 2003, Pages 7537-7540

  Marugg, Jennifer L ^a   Neitzel, Martin L ^a   Tucker, John ^a  

^a ELAN PHARMACEUTICALS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 BIPHENYL(TERT BUTYL) 2 PHOSPHINE; PHOSPHINE DERIVATIVE; SULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; SOLID; SYNTHESIS;

EID: 0041333879     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.07.004     Document Type: Article

References (14)

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3. Wolfe J.P., Buchwald S.L. Angew. Chem., Int. Ed. 38:1999;2413-2415.
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5. Littke A.F., Dai C., Fu G.C. J. Am. Chem. Soc. 122:2000;4020-4028.
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10. Bio-Rad AG® 50W-X2 200-400 mesh hydrogen form resin was washed with methanol and dried under vacuum at room temperature prior to use.
11. The absorption of 1 onto sulfonic acid resins presumably results from proton transfer from the sulfonic acid group to the basic phosphorus atom, followed by ion pairing of the phosphonium ion with the polymer-supported sulfonate group. In acetonitrile, the basicity of tri(t-butyl)phosphine is similar to that of morpholine, while that of triphenylphosphine is roughly similar to that of 4-(trifluoromethyl)aniline. Abdur-Rashid, K.; Fong, T. P.; Greaves, B.; Gusev, D. G.; Hinman, J. G.; Landau, S. E.; Lough, A. J.; Morris, R. H. J. Am. Chem. Soc. 2000, 122, 9155-9171.
12. Miyaura N., Suzuki A. Chem. Rev. 95:1995;2457.
13. Suzuki A. J. Organomet. Chem. 576:1999;147.
14. 2, 12 mg (0.04 mmol) of 2-(di-t-butylphosphino)biphenyl, 73 mg (0.6 mmol) of phenylboronic acid, and 70 mg (1.2 mmol) of KF in 2 mL of THF under nitrogen was treated with 45 uL (0. 4 mmol) of 3-chloropyridine. The mixture was agitated for 14 h at 25°C and then it was filtered through a 13 mm PTFE syringe filter into an 8 mL vial. The solution was diluted with 5 mL of THF and then it was treated with 3.1 g (2.38 mmol) of Silicycle® sulfonic acid resin. The mixture was agitated for 1 h, filtered, and the resin was washed with 2 mL of methanol. The resin was treated with 7 mL of 5% methanolic pyridine (3.2 mmol) and the mixture was agitated for 10 min. The mixture was filtered and the resin was washed with 5 mL of 5% methanolic pyridine. Evaporation of the solvent gave an 88% yield of the known compound 3-phenylpyridine having >95% purity (LC-MS). Subsequent treatment of the resin with 2 M methanolic ammonia led to recovery of the ligand in 71% yield and >95% purity.