Herrmann-Beller phosphapalladacycle-catalyzed addition of alkynes to norbornadienes

Organic Letters

Volumn 8, Issue 19, 2006, Pages 4315-4318

  Tenaglia, Alphonse ^a   Giordano, Laurent ^a   Buono, Gérard ^a  

^a EGIM   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748991433     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061667e     Document Type: Article

References (50)

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42. The propensity to form η-1-allenylpalladium(II) complexes from zerovalent palladium and propargyl acetate 3h or carbonate 3k also ruled out Pd(O) species as active catalyst from 1.
43. We thank one of the referees for useful comments regarding the mechanism.
44. Similar observations have been reported for the palladium-catalyzed [2 + 1] cycloaddition of terminal alkynes with norbornenes. See: Bigeault, J.; Giordano, L.; Buono, G. Angew. Chem., Int. Ed. 2005, 44, 4753-4757.
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46. Typical Experimental Procedure. Norbornadiene 2 (184 mg, 2 mmol) and phenylethyne 3a (102 mg, 1 mmol) in DCE (6 mL) were added to a solution of palladium catalyst 1 (23.5 mg, 0.025 mmol) in DCE (2 mL). The mixture was stirred at 55°C for 20 h, cooled at room temperature, and concentrated in vacuo. The crude product was purified by chromatography on silica gel (hexanes) to yield 175 mg (90% yield) of exo-5-(phenylethynyl)-2-norbornene (4a).
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