M. B. Andrus et al. / Tetrahedron Letters 43 (2002) 9137–9140
Table 3. p-Bromo, nitro, and 2-naphthyl coupling
9139
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9. An autoclave with a pressure gauge was used.
1
0. Aryl diazonium ions were formed using the procedure
of: Doyle, M. P.; Siegfreid, B.; Elliot, R. C.; Dellaria, J.
F. J. Org. Chem. 1977, 42, 2431.
11. General procedure: Aryldiazonium tetrafluoroborate
(
(
0.250 mmol), arylboronic acid (0.250 mmol), Pd(OAc)2
0.91 mg, 0.002 mmol, 2 mol%) and N,N-bis-(2,6-diiso-
propylphenyl)-4,5-dihydroimidazolium chloride (1.70
mg, 0.002 mmol, 2 mol%) were mixed under nitrogen in
a round bottom flask. Anhydrous dioxane (2 mL) was
added and the flask was charged with CO (1 atm). The
resulting suspension was stirred at reflux temperature for
5
h. The reaction mixture was cooled and methylene
chloride (10 mL) was added. The solution was washed
three times with aqueous brine and dried over anhy-
drous magnesium sulfate. The solvent was removed by
rotary evaporation and the mixture was purified by sil-
1
ica gel chromatography. Adequate characterization ( H
isolated yields. In many cases only very small amounts
of non-carbonylative biaryl coupling was observed.
Electron-deficient diazonium ions are particularly
efficient. The versatility of the conditions will be further
developed and applied to more complex targets.
NMR, MS) for the ketone products, all of which are
known, was obtained. Representative examples and data
follows:
Benzophenone: Yield: 71%, R : 0.55 (10% EtOAc/hex-
f
1
anes); H NMR (CDCl ): l 7.33–7.68 (m, 10H); MS
3
(
EI) m/z 180.
Chalcone: Yield: 49%, R : 0.45 (10% EtOAc/hexanes);
f
1
Acknowledgements
H NMR (CDCl ): l 7.08–7.69 (m, 11H), 6.81 (d, 1H,
3
J=6.8); MS (EI) m/z 208.
We are grateful for support provided by Brigham
Young University, Shandong University and the
National Institutes of Health (GM57275).
4-t-Butylbenzophenone: Yield: 75%, Rf: 0.40 (10%
1
EtOAc/hexanes); H NMR (CDCl ): l 7.30–7.67 (m,
3
9H), 1.32 (s, 9H); MS (EI) m/z 238.