Abstract
Cross-coupling reactions of hypervalent organobismuth compounds, 6-tert -butyl-5,6,7,12-tetrahydrodibenz[c ,f ][1,5]azabismocines, with aryl and alkenyl chlorides are efficiently catalyzed by the Pd(OAc)2 /dppf [dppf = 1,1′-bis(diphenylphosphino)ferrocene] system.
Key words
cross-coupling - organometallic reagents - bismuth - palladium - hypervalent
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Typical Procedure: A mixture of 2a (161 mg, 0.30 mmol), 4-CF3 C6 H4 Cl (46 mg, 0.25 mmol), Pd(OAc)2 (5.6 mg, 0.025 mmol) and dppf (14 mg, 0.025 mmol) in 3 mL of NMP was heated at 100 °C for 12 h under N2 . The crude mixture was dissolved in EtOAc (90 mL) and washed with aq HCl (4 M, 3 × 10 mL) and H2 O (10 mL). The organic layer was dried over Na2 SO4 , filtered, and concentrated in vacuo. The residue was separated with a short pad of silica gel, eluting with EtOAc-hexane (1:10) to give a mixture containing cross-coupled product and then with CH2 Cl2 -EtOAc (1:1) to give pure 2e (145 mg, 98%). The former mixture was further purified with PTLC to give 4-trifluoromethylbiphenyl (45 mg, 79%).
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13b Oxidative addition of 1 toward Pt(PEt3 )3 takes place even at -50 °C and is complete within 1 h at 0 °C, while that of 2a toward Pt(PEt3 )3 is slow at r.t. and is not complete, and seems to reach equilibrium at about 60% conversion.
