Palladium-Catalyzed Cross-Coupling Reaction of Organobismuth Compounds with Aryl and Alkenyl Chlorides

Osamu Yamazaki; Toshifumi Tanaka; Shigeru Shimada; Yohichi Suzuki; Masato Tanaka

doi:10.1055/s-2004-831298

LETTER

Palladium-Catalyzed Cross-Coupling Reaction of Organobismuth Compounds with Aryl and Alkenyl Chlorides

Osamu Yamazaki^a, Toshifumi Tanaka^b, Shigeru Shimada*^a, Yohichi Suzuki^b, Masato Tanaka*^a,c
^a National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba, Ibaraki 305-8565, Japan
^b Department of Industrial Chemistry, College of Industrial Technology, Nihon University, Narashino, Chiba 275-8575, Japan
^c Chemical Resources Laboratory, Tokyo Institute of Technology, Nagatsuta, Midori-ku, Yokohama 226-8503, Japan
Fax: +81(29)8614511; e-Mail: s-shimada@aist.go.jp;

Abstract

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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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References

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Typical Procedure: A mixture of 2a (161 mg, 0.30 mmol), 4-CF₃C₆H₄Cl (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 H₂O (10 mL). The organic layer was dried over Na₂SO₄, 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 CH₂Cl₂-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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The ³¹P NMR spectrum of each of the mixture at r.t. showed a broad signal suggesting a rapid exchange of coordinated and uncoordinated PPh₃. The signals shifted upfield gradually and reached that of free PPh₃ after complete decomposition.

Shimada, S.; Tanaka, M. unpublished results.

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.