Nickel- and palladium-catalyzed cross-coupling reaction of polyfluorinated arenes and alkenes with grignard reagents

Synlett

Volumn , Issue 11, 2005, Pages 1771-1774

  Saeki, Tomoyuki ^a   Takashima, Yohei ^a   Tamao, Kohei ^a,b  

^a KYOTO UNIVERSITY   (Japan)

^b Japan Science and Technology Agency   (Japan)

Author keywords

Cross coupling; Fluoroarene; Grignard reagent; Nickel; Palladium

Indexed keywords

1,2 DIFLUOROBENZENE; ALKENE; FLUOROBENZENE; GRIGNARD REAGENT; NICKEL; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON; REAGENT; TRIFLUOROBENZENE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; FLUORINATION;

EID: 22244431897     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-871571     Document Type: Article

References (44)

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36. Ligand abbreviation: dppp = 1,3-bis(diphenylphosphino)propane, dppb = 1,4-bis(diphenylphosphino)butane, and dppf = 1,1′-bis(di-phenylphosphino) ferrocene.
37. 4Sn, trace.
38. 4MgBr (2, 1.0 M THF solution; 1.5 mL, 1.5 mmol) at r.t. and the mixture was heated under reflux for 48 h. The reaction was monitored by GC analysis with eicosane (54 mg) as an internal standard to reveal that the reaction completed within 48 h and 2-fluoro-4′-methylbiphenyl (5a) was formed in 91% yield. The further purification was performed with column chromatography on silica gel and high performance liquid chromatography (HPLC).
39. 6): δ = 2.16 (s, 6 H), 7.00 (t, J = 7.5 Hz, 1 H), 7.08 (d, J = 8.1 Hz, 4 H), 7.27 (dd, J = 7.5, 7.2 Hz, 2 H), 7.52 (d, J = 8.1 Hz, 4 H).
40. 6): δ = 2.18 (s, 6 H), 7.06 (d, J = 7.8 Hz, 4 H), 7.26 (dd, J = 9.6, 1.5 Hz, 2 H), 7.37 (d, J = 7.8 Hz, 4 H), 7.64 (t, J = 1.5 Hz, 1 H).
41. 6): δ = 2.13 (s, 3 H), 6.61 (tdd, J = 8.1, 4.8, 1.5 Hz, 1 H), 6.73 (dddd, J = 9.9, 8.1, 7.2, 1.5 Hz, 1 H), 6.89 (ddt, J = 8.1, 6.3, 1.5 Hz, 1 H), 7.02 (d, J = 7.8 Hz, 2 H), 7.35 (dd, J = 8.1, 1.8 Hz, 2 H).
42. 6): δ = 2.12 (s, 3 H), 6.89 (d, J = 37.2 Hz, 1 H), 7.01 (d, J = 8.7 Hz, 2 H), 7.33-7.38 (m, 3 H), 7.56 (d, J = 8.7 Hz, 2 H), 7.62 (d, J = 8.4 Hz, 1 H), 7.69-7.72 (m, 1 H), 8.02-8.05 (m, 1 H), 8.08 (d, J = 7.2 Hz, 1 H).
43. 6): δ = 2.01 (s, 3 H), 2.20 (s, 3 H), 6.80 (d, J = 8.0 Hz, 2 H), 7.05 (dd, J = 8.4, 8.1 Hz, 1 H), 7.08 (d, J = 8.1 Hz, 2 H), 7.16 (d, J = 8.0 Hz, 2 H), 7.30-7.34 (m, 3 H), 7.46 (d, J = 8. 1 Hz, 2 H), 7.45-7.49 (m, 1 H), 7.51 (s, 1 H), 7.65-7.69 (m, 1 H), 8.10-8.13 (m, 1 H).
44. 6): δ = 1.88 (s, 3 H), 6.64 (d, J = 8.1 Hz, 2 H), 6.86 (d, J = 21.0 Hz, 1 H), 7.09 (dd, J = 8.1, 7.5 Hz, 1 H), 7.28-7.32 (m, 3 H), 7.31 (d, J = 8.1 Hz, 2 H), 7.56 (d, J = 7.5 Hz, 1 H), 7.63-7.69 (m, 1 H), 7.98-8.03 (m, 1 H).