Phospha-adamantanes as ligands for organopalladium chemistry: Aminations of aryl halides

Tetrahedron Letters

Volumn 45, Issue 45, 2004, Pages 8319-8321

  Gerristma, David ^a   Brenstrum, Timothy ^a   McNulty, James ^a   Capretta, Alfredo ^a  

^a MCMASTER UNIVERSITY   (Canada)

Author keywords

Amination; Organopalladium chemistry; Phosphine ligand

Indexed keywords

1,3,5,7 TETRAMETHYL 2,4,8 TRIOXA 6 PHENYL 6 PHOSPHADAMANTANE; ADAMANTANE DERIVATIVE; ALIPHATIC AMINE; AROMATIC AMINE; HALIDE; LIGAND; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CHEMISTRY; GAS CHROMATOGRAPHY; MASS SPECTROMETRY;

EID: 5144230656     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.09.067     Document Type: Article

References (23)

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16. 3 (2%, 20.7 mg, 0.02 mmol), 1,3,5,7-tetramethyl-2,4,8-trioxa-6-phenyl-6-phospha-adamantane (4%, 11.7 mg, 0.04 mmol), sodium tert-butoxide (144 mg, 1.5 mmol), the amine (1.2 mmol) and the aryl halide (1.0 mmol) were stirred in toluene (dry, degassed, 1.5 mL) under an argon atmosphere and heated (at 30°C for aryl iodides, 50°C for aryl bromides or 70°C for aryl chlorides). Note that elevated temperatures are required for couplings involving aniline (90°C for bromides and 110°C for chlorides). The reaction was monitored via TLC and after the appropriate amount of time, the reaction was then diluted with diethyl ether (10 mL), washed with distilled water (1 × 10 mL) and brine (1 × 10 mL). The organic solution was concentrated under reduced pressure and the residue purified via flash silica gel chromatography.
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23. 3, 75 MHz) δ 11.4, 20.2, 52.7, 96.3, 111.1, 121.0, 133.6, 150.7