Chromatography-free Pd-catalyzed deprotection of allyl ethers using PS-DEAM as a scavenger of boronic acids and Pd catalyst

Tetrahedron Letters

Volumn 48, Issue 48, 2007, Pages 8438-8441

  Tsukamoto, Hirokazu ^a   Suzuki, Takamichi ^a   Sato, Masanori ^a   Kondo, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

4 (DIPHENYLPHOSPHINO)BENZOIC ACID; ALLYL ETHER; BENZENEBORONIC ACID; BENZOIC ACID DERIVATIVE; DIETHANOLAMINE; ETHER DERIVATIVE; PALLADIUM; POLYSTYRENE; PYRIDINE DERIVATIVE; SCAVENGER; UNCLASSIFIED DRUG; VINYLBORONIC ANHYDRIDE PYRIDINE COMPLEX;

ALLYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DEPROTECTION REACTION; EVAPORATION;

EID: 35548994470     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.10.001     Document Type: Article

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33. PS-DEAM and MP-TMT were purchased from Argonaut technologies.
34. 4 (2.5 mg, 2.2 μmol) was added anhydrous THF (1.0 mL) under argon. The resulting mixture was sealed with a screw cap and agitated at 80 °C for 12 h. The mixture was cooled down to room temperature, and then PS-DEAM™ (1.7 mmol/g, 0.53 g, 0.90 mmol) and THF (5.3 mL) were added to the mixture. The mixture was agitated at room temperature for 24 h. The mixture was filtered and thoroughly washed with THF. The filtrate was concentrated in vacuo and residue 5a was dissolved in 1,4-dioxane, ultra pure water, and aqua regia (10 mL) and subjected to ICP-ES. The reduction in Pd was calculated on the basis of the residual Pd concentration determined by ICP-ES.
35. Si-TAAcOH and Si-thiourea were purchased from SILICYCLE.
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40. Vinylboronic anhydride pyridine complex and 4-(diphenylphosphino)benzoic acid were purchased from Aldrich.
41. + 194.0943, found 194.0945.
42. For complete conversion of 4 to 5, this catalytic system requires higher catalyst loading and longer reaction time than the former. The work-up consisting of agitation with PS-DEAM, filtration, and evaporation must be repeated twice for complete conversion of partially formed borates 6 to free alcohols 5. PS-DEAM might capture 5 partially as its borate and decrease isolated yield of 5 slightly.
43. 2 in anhydrous THF (6.0 mM, 0.38 mL, 2.3 μmol) under argon. The resulting mixture was sealed with a screw cap and agitated at 80 °C for 12 h. The mixture was cooled down to room temperature, and then PS-DEAM™ (1.8 mmol/g, 0.25 g, 0.45 mmol) and THF (2.5 mL) were added to the mixture. The mixture was agitated at room temperature for 12 h. The mixture was filtered and thoroughly washed with THF. The filtrate was concentrated in vacuo and the residue was subjected to the above PS-DEAM treatment again to give 5a (39.0 mg, 0.216 mmol, 96%). The reduction in Pd was calculated on the basis of the residual Pd concentration determined by ICP-ES.