Angewandte
Chemie
Table 1: (Continued)
[7] A. C. Frisch, N. Shaikh, A. Zapf,
M. Beller, Angew.Chem. 2002,
114, 4218 – 4221; Angew.Chem.
Int.Ed. 2002, 41, 4056 – 4059.
Entry
Substrate
RMgX/RLi
PhMgBr
Product
Yield [%]
85[b]
[8] The following recent publications
report iron-catalyzed arylations of
33
alkyl halides using structurally
undefined catalysts formed “in
situ”: a) M. Nakamura, K.
34
PhMgBr
77[h]
Matsuo, S. Ito, E. Nakamura, J.
Am.Chem.Soc. 2004, 126, 3686 –
3687; b) T. Nagano, T. Hayashi,
Org.Lett. 2004, 6, 1297 – 1299.
[a] Only 1 mol% of complex 1 was used. [b] The reaction was performed at 08C. [c] After hydrolytic work-
up. [d] Using 2 equiv of PhMgBr. [e] 15:1 mixture with 1,1-diphenylallene. [f] 5:1 mixture with 1-phenyl-1-
trimethylsilylallene. [g] No allene by-product detected in the crude mixture. [h] No incorporation of the
phenyl group was observed.
[9] J. K. Kochi, Acc.Chem.Res. 1974,
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[10] a) A. Fürstner, A. Leitner, M.
MØndez, H. Krause, J.Am.
standard extractive work-up and flash chromatography (hexanes/
ethyl acetate 4:1) of the crude product afforded 2-benzoyl-6-phenyl-
2-(4-phenyl-but-2-enyl)-hex-4-enoic acid ethyl ester as a colorless
solid (217 mg, 96%). 1H NMR (CDCl3, 400 MHz): d = 0.92(t, J =
6.8 Hz, 3H), 1.98 (m, 2H), 2.37 (m, 2H), 3.44 (m, 2H), 3.89 (m, 4H),
4.61 (d, J = 6.2Hz, 2H), 5.23 (m, 2H), 7.31 ppm (m, 15H); 13C NMR
(CDCl3, 100 MHz): d = 13.6, 30.8, 30.9, 52.8, 52.9, 60.3, 60.4, 77.8, 77.9,
124.86, 124.9, 125.0, 126.3, 126.6, 127.8, 127.9, 128.7, 128.8, 143.6,
143.7, 146.7, 175.8, 175.8 ppm; IR (film): n˜ = 3066, 2941, 1771, 1743,
1646, 1617, 1448, 1265, 1150, 1048, 906, 791 cmÀ1; elemental analysis
calcd for C31H32O3: C 82.27, H 7.13; found: C 82.35, H 7.30.
Chem.Soc. 2002, 124, 13856 – 13863; b) A. Fürstner, A. Leitner,
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[14] B. Scheiper, F. Glorius, A. Leitner, A. Fürstner, Proc.Natl.Acad.
Sci.USA , in press.
Received: April 29, 2004 [Z460504]
Published Online: July 7, 2004
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Keywords: alkyl halides · cross-coupling · Grignard reagents ·
iron
.
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ꢀ 2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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