RESEARCH FRONT
Reactions of Organogold Compounds with Electrophiles
1625
495%. dH (CDCl3, 250 MHz) 7.24–7.17 (m, 5H). m/z (GC-MS)
(m) Z. G. Li, C. Brouwer, C. He, Chem. Rev. 2008, 108, 3239.
doi:10.1021/CR068434L
103.0 (M)þ.
(n) A. S. K. Hashmi, Aldrichimica Acta 2010, 43, 27.
[2] A. S. K. Hashmi, M. Rudolph, Chem. Soc. Rev. 2008, 37, 1766.
doi:10.1039/B615629K
4,40-Dimethoxy-1,10-biphenyl (4g) (Chart 29)
[3] (a) A. S. K. Hashmi, Angew. Chem. 2010, 122, 5360. doi:10.1002/
ANGE.200907078
MeO
OMe
(b) A. S. K. Hashmi, Angew. Chem. Int. Ed. 2010, 49, 5232. doi:10.1002/
ANIE.200907078
Chart 29.
[4] (a) For such examples, see: A. S. K. Hashmi, S. Pankajakshan,
M. Rudolph, E. Enns, T. Bander, F. Rominger, W. Frey, Adv. Synth.
Catal. 2009, 351, 2855. doi:10.1002/ADSC.200900614
(b) A. S. K. Hashmi, M. Rudolph, J. Huck, W. Frey, J. W. Bats,
M. Hamzic, Angew. Chem. 2009, 121, 5962. doi:10.1002/ANGE.
200900887
To Selectfluor (26.0 mg, 74.0 mmol, 1.05 eq) in acetonitrile
(5 mL) was added 4-methoxyphenyl(triphenylphosphan)gold
(40.0 mg, 71.0 mmol, 1.00 eq) and stirred at room temperature
for 1 h. The reaction mixture was adsorbed onto silica and
purified by flash column chromatography (20% ethyl acetate in
petroleum ether) to give the product as a white solid (8.0 mg,
94%). The NMR data is in accordance with literature data.[24] dH
(CDCl3, 250 MHz) 7.48 (d, J 8.78, 4H), 6.96 (d, J 8.79, 4H), 3.85
(s, 6H). m/z (EIþ) 214 (100%) [M]þ. Spectroscopic data match
those in the literature.[1]
(c) A. S. K. Hashmi, M. Rudolph, J. Huck, W. Frey, J. W. Bats,
M. Hamzic, Angew. Chem. Int. Ed. 2009, 48, 5848. doi:10.1002/
ANIE.200900887
(d) A. S. K. Hashmi, S. Scha¨fer, M. Wo¨lfle, C. Diez Gil, P. Fischer,
A. Laguna, M. C. Blanco, M. C. Gimeno, Angew. Chem. 2007, 119,
6297. doi:10.1002/ANGE.200701521
(e) A. S. K. Hashmi, S. Scha¨fer, M. Wo¨lfle, C. Diez Gil, P. Fischer,
A. Laguna, M. C. Blanco, M. C. Gimeno, Angew. Chem. Int. Ed. 2007,
46, 6184. doi:10.1002/ANIE.200701521
4,40-Dimethyl-2,20-di(propan-2-yl)-3,30-bifuran-
5,50(2H,20H)-dione (4h)
(f) A. S. K. Hashmi, M. Rudolph, H.-U. Siehl, M. Tanaka, J. W. Bats,
W. Frey, Chem. Eur. J. 2008, 14, 3703. doi:10.1002/CHEM.
200701795
To a solution of ethyl 2,5-dimethylhexa-2,3-dienoate (KG-26)
in acetonitrile, one equivalent of gold(III) trichloride was added
and the reaction mixture was stirred for 6 h at 808C. The product
formed was purified via column chromatography on silica with
petrol ether and ethyl acetate as eluents. Yield: 76% as a mixture
of two diastereomers.
[5] (a) C. M. Krauter, A. S. K. Hashmi, M. Pernpointner, ChemCatChem
2010, 2, 1226. doi:10.1002/CCTC.201000136
(b) A. S. K. Hashmi, Catal. Today 2007, 122, 211. doi:10.1016/
J.CATTOD.2006.10.006
(c) A. S. K. Hashmi, L. Schwarz, P. Rubenbauer, M. C. Blanco, Adv.
Synth. Catal. 2006, 348, 705. doi:10.1002/ADSC.200505464
[6] (a) J. P. Weyrauch, A. S. K. Hashmi, A. Schuster, T. Hengst,
S. Schetter, A. Littmann, M. Rudolph, M. Hamzic, J. Visus,
F. Rominger, W. Frey, J. W. Bats, Chem. Eur. J. 2010, 16, 956.
doi:10.1002/CHEM.200902472
Diastereomer 1: dH (CD3CN, 300 MHz) 0.72 (d, J 6.89, 3H),
1.15 (d, J 6.89, 3H), 1.85 (s, 3H), 1.78 (s, 3H), 2.05 (m, 1H), 4.92
(m, 1H). dC (CD3CN, 75 MHz) 10.37 (q), 14.09 (q), 20.04 (q),
30.08 (d), 86.19 (d), 130.06 (s), 151.82 (s), 173.68 (s).
Diastereomer 2: dH (CD3CN, 300 MHz) 0.64 (d, J 6.89, 3H),
1.12 (d, J 6.89, 3H), 1.79 (s, 3H), 1.85 (s, 3H), 2.04 (m, 1H), 5.06
(m, 1H). dC (CD3CN, 75 MHz) 11.19 (q), 14.60 (q), 21.16 (q),
31.40 (d), 86.97 (d), 130.80 (s), 152.49 (s), 173.89 (s).
(b) S. F. Kirsch, J. T. Binder, B. Crone, A. Duschek, T. T. Haug,
C. Lie´bert, H. Menz, Angew. Chem. Int. Ed. 2007, 46, 2310.
doi:10.1002/ANIE.200604544
(c) M. Yu, G. Zhang, L. Zhang, Org. Lett. 2007, 9, 2147. doi:10.1021/
OL070637O
Acknowledgement
(d) B. Crone, S. F. Kirsch, J. Org. Chem. 2007, 72, 5435. doi:10.1021/
JO070695N
(e) A. Buzas, F. Gagosz, Org. Lett. 2006, 8, 515. doi:10.1021/
OL053100O
This work was supported by the Deutsche Forschungsgemeinschaft
(SFB 623). A.S.-K.T. thanks the DAAD for a fellowship. We are grateful to
Umicore AG & Co. KG for the donation of gold salts.
(f) A. Buzas, F. Gagosz, Synlett 2006, 2727. doi:10.1055/S-2006-
950253
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