Home
  >  
Section 53
  >  
Chapter 52,912

Efficient synthesis of sterically crowded biaryls by palladium-phosphinous acid-catalyzed cross-coupling of aryl halides and aryl grignards

Wolf, C.; Xu, H.

Journal of Organic Chemistry 73(1): 162-167

2008

ISSN/ISBN: 0022-3263
PMID: 18052388
DOI: 10.1021/jo701893m
Accession: 052911324
Download citation:  
Text
  |  
BibTeX
  |  
RIS
A series of sterically hindered biaryls have been obtained by palladium- and nickel-phosphinous acid-catalyzed Kumada-Corriu cross-coupling of ortho-substituted aryl halides and Grignard reagents. This method allows formation of di- and tri-ortho-substituted biaryls in 87-98% yield under mild reaction conditions even when electron-rich aryl chlorides are used. The reaction also proceeds with aryl iodides at -20 degrees C, and under these conditions, functional groups that are generally not compatible with Grignard reagents are tolerated.

PDF emailed within 0-6 h: $19.90




Related References

Xu, H.; Ekoue-Kovi, K.; Wolf, C. 2008: Palladium-phosphinous acid-catalyzed cross-coupling of aryl and acyl halides with aryl-, alkyl-, and vinylzinc reagents Journal of Organic Chemistry 73(19): 7638-7650
Su, W.; Urgaonkar, S.; McLaughlin, P.A.; Verkade, J.G. 2004: Highly active palladium catalysts supported by bulky proazaphosphatrane ligands for Stille cross-coupling: coupling of aryl and vinyl chlorides, room temperature coupling of aryl bromides, coupling of aryl triflates, and synthesis of sterically hindered biaryls Journal of the American Chemical Society 126(50): 16433-16439
Wu, Q.; Jin, R.; Kang, C.; Chen, W.; Bian, Z.; Ma, X.; Ding, J.; Guo, H.; Qiu, X.; Gao, L. 2016: Ni-Catalyzed cross coupling of aryl grignard reagents with aryl halides in a nonpolar solvent and an efficient synthesis of biaryls under neat conditions Chemical Research in Chinese Universities 32(1): 55-61
Deng, C.; Guo, S.; Xie, Y.; Li, J. 2007: Mild and Ligand-Free Palladium-Catalyzed Cross-Couplings between Aryl Halides and Arylboronic Acids for the Synthesis of Biaryls and Heterocycle-Containing Biaryls European Journal of Organic Chemistry 9: 1457-1462
Hassan, J.; Hathroubi, C.; Gozzi, C.; Lemaire, M. 2000: Synthesis of unsymmetrical biaryls via palladium-catalyzed coupling reaction of aryl halides Tetrahedron Letters 41(45): 8791-8794
Lehmann, U.; Awasthi, S.; Minehan, T. 2003: Palladium-catalyzed cross-coupling reactions between dihydropyranylindium reagents and aryl halides. synthesis of C-aryl glycals Organic Letters 5(14): 2405-2408
Jørgensen, M.; Lee, S.; Liu, X.; Wolkowski, J.P.; Hartwig, J.F. 2002: Efficient synthesis of alpha-aryl esters by room-temperature palladium-catalyzed coupling of aryl halides with ester enolates Journal of the American Chemical Society 124(42): 12557-12565
Chen, J.; Zhang, Y.; Hao, W.; Zhang, R.; Yi, F. 2013: Efficient synthesis of aryl hydrazines using copper-catalyzed cross-coupling of aryl halides with hydrazine in PEG-400 Tetrahedron 69(2): 613-617
Gomes, P.; Fillon, H.; Gosmini, C.; Labbé, E.; Périchon, J. 2002: Synthesis of unsymmetrical biaryls by electroreductive cobalt-catalyzed cross-coupling of aryl halides Tetrahedron 58(42): 8417-8424
Amatore, C.; Carré, E.; Jutand, A.; Tanaka, H.; Ren, Q.; Torii, S. 1996: Oxidative Addition of Aryl Halides to Transient Anionic à-Aryl- “Palladium(0) Intermediates- Application to Palladium-Catalyzed Reductive Coupling of Aryl Halides Chemistry - A European Journal 2(8): 957-966
Xu, H.; Fan, L.-L. 2008: Synthesis of dibenzofurans directly from aryl halides and ortho-bromophenols via one-pot consecutive SNAr and intramolecular palladium-catalyzed aryl-aryl coupling reactions Chemical and Pharmaceutical Bulletin 56(10): 1496-1498
Bose, S.K.; Marder, T.B. 2014: Efficient synthesis of aryl boronates via zinc-catalyzed cross-coupling of alkoxy diboron reagents with aryl halides at room temperature Organic Letters 16(17): 4562-4565
Bailey, T.R. 1986: Unsymmetrical heterobiaryl synthesis. A high efficient palladium-catalyzed cross-coupling reaction of heteroaryl trialkylstannanes with aryl halides Tetrahedron Letters 27(37): 4407-4410
Dankwardt, J.W. 2005: Transition metal catalyzed cross-coupling of aryl Grignard reagents with aryl fluorides via Pd- or Ni-activation of the C–F bond: an efficient synthesis of unsymmetrical biaryls – application of microwave technology in ligand and catalyst screening Journal of Organometallic Chemistry 690(4): 932-938
Lee, D.; Ryu, T.; Park, Y.; Lee, P.H. 2014: Unmasked acyl anion equivalent from acid chloride with indium: reversed-polarity synthesis of unsymmetric aryl aryl and alkenyl aryl ketone through palladium-catalyzed cross-coupling reaction Organic Letters 16(4): 1144-1147
Wolf, C.; Lerebours, R. 2004: Palladium-phosphinous acid-catalyzed NaOH-promoted cross-coupling reactions of arylsiloxanes with aryl chlorides and bromides in water Organic Letters 6(7): 1147-1150
Hatanaka, Y.; Fukushima, S.; Hiyama, T. 1989: Selective Synthesis of Unsymmetrical Biaryls via Palladium-Catalyzed Cross-Coupling of Arylfluorosilanes with Aryl Iodides Chemistry Letters 18(10): 1711-1714
Hudkins, R.L.; Diebold, J.L.; Marsh, F.D. 1995: Synthesis of 2-Aryl- and 2-Vinyl-1H-indoles via Palladium-Catalyzed Cross-Coupling of Aryl and Vinyl Halides with 1-Carboxy-2-(tributylstannyl)indole The Journal of Organic Chemistry 60(19): 6218-6220
Kalinin, V.; Min, S.F. 1988: Synthesis of aryl- and vinyl-sydnones. Cross-coupling of 4-copper-3-phenylsydnone with aryl and vinyl halides catalyzed by palladium(0) complexes Journal of Organometallic Chemistry 352(1-2): C34-C36
Youhua, Y.A.N.G.; Martin, A.R. 1992: Synthesis of 5-arylated indoles via palladium-catalyzed cross-coupling reaction of 5-indolylboronic acid with aryl and heteroaryl-halides Heterocycles (Sendai) 34(7): 1395-1398