Cationic lr(l)-catalyzed sp3 C- H bond alkenylation of amides with alkynes

Organic Letters

Volumn 11, Issue 8, 2009, Pages 1821-1823

  Tsuchikama, Kyoji ^a   Kasagawa, Mitsugu ^a   Endo, Kohei ^a   Shibata, Takanori ^a  

^a WASEDA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 65249146748     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900404r     Document Type: Article

References (31)

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28. 2]OTf (5.7 mg, 10 μmol) and rac-BINAP (6.8 mg, 11 μmol) were placed in a Schlenk tube, which was then evacuated and backfilled with argon (×3). To the reaction vessel were added N,N-dimethyrbenzamide (la) (15.0 mg, 0.1 mmol), diphenylacetylene (2a) (36.6 mg,'o.2 mmol), and PhCl (0.2 mL). The solution was then stirred at 135 °C for 24 h. After completion of the reaction, the solvent was evaporated. The crude products were purified by thin-layer chromatography (hexane/AcOEt = 1/1) to give analytically pure 3aa (75%) and 3aa (4%),
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31. 2O (3 equiv) were heated in the presence of lr(I)-BINAP catalyst, the deuteration ratio at the allylic position decreased to 37%-D.