In Situ Generated Rhodium-Based Catalyst for Addition of Phenylboronic Acid to Aldehydes 465
General Procedure for Rhodium-Carbene
Catalyzed Addition of Phenylboronic Acid
to Aldehydes
[10] (a) Doyle, M. J.; Lappert, M. F.; Pye, P. L.; Terreros, P.
J Chem Soc, Dalton Trans 1984, 2355–2364; (b) Cole-
man, A. W.; Hitchcock, P. B.; Lappert, M. F.; Maskell,
R. K.; M u¨ ller, J. H. J Organomet Chem 1985, 296,
1
73–176; (c) Cetinkaya, B.; Hitchcock, P. B.; Lappert,
Phenylboronic acid (1.20 g, 9.8 mmol), KOtBu
M. F.; Shaw, D. B.; Spyropoulos, K.; Warhurst, N. J.
W. J Organomet Chem 1993, 459, 311–317.
(
[
(
4.9 mmol), substituted aldehydes (4.9 mmol),
RhCl(COD)] (1 mmol %), imidazolinium salts
2 and 4) (2 mmol), dimethoxyethane (15 mL)
2
[
11] (a) Bourissou, D.; Guerret, O.; Gabbai, F. P.; Bertrand,
G. Chem Rev 2000,100, 39–92; (b) Arduengo, A. J Acc
Chem Res 1999, 32, 913–921; (c) Enders, D.; Gielen,
H. J Organomet Chem 2001, 70, 617–618; (d) Crud-
den, C. M.; Allen, D. P. Coord Chem Rev 2004, 248,
were introduced in to Schlenk tube and then water
(
5 mL) was added. The resulting mixture was stirred
◦
room temperature or heated for 5 h at 60 C, cooled
to ambient temperature, exracted with ethyl acetate
2
247–2273.
¨
[
[
12] (a) Ozdemir, I.; Yi g˘ it, M.; C¸ etinkaya, E.; C¸ etinkaya, B.
Tetrahedron Lett 2004, 45, 5823–5825; (b) G u¨ rb u¨ z,
N.; Ozdemir, I.; C¸ etinkaya, B. Tetrahedron Lett 2005,
4
13] (a) Miyaura, N.; Suzuki, A. Chem Rev 1995, 95, 2457–
(
30 mL). After drying over MgSO the organic phase
4
¨
was evaporated and the residue was purified by flash
chromatography. Isolated yield (yields based on alde-
hydes) is checked by NMR, all reactions were moni-
tored by TLC.
6, 2273–2277.
¨
483; (b) Ozdemir, I.; Demir, S.; Y s¸ ar, S.; C¸ etinkaya,
2
B. Appl Organomet Chem 2005, 19, 55–58.
14] Bielowski, C. W.; Grubbs, R. H. Angew. Chem, Int. Ed.
Engl 2000, 39, 2903–2906.
15] (a) Stauffer, S. R.; Lee, S.; Stambouli, J. P.; Hanck,
S. I.; Hartwig, J. F. Org Lett 2000, 2, 1423–1426;
(b) Ozdemir, I.; Demir, S.; G o¨ k, Y.; C¸ etinkaya, E.;
C¸ etinkaya, B. J Mol Catal A 2004, 222, 97–102.
[16] C¸ etinkaya, B.; Ozdemir, I.; Dixneuf, P. H. J Organomet
Chem 1997, 534, 153–158.
[17] (a) C¸ etinkaya, B.; Demir, S.; Ozdemir, I.; Toupet,
[
[
REFERENCES
¨
[
1] (a) Parshal, G. W.; Ittel, S. D. Homogeneous Catal-
ysis.; 2nd ed.; Wiley : New York, 1992; (b) Cornils,
B.; Hermann, W. A. Applied Homogeneous Catalysis
with Organometallic Compounds.; VCH: New York,
¨
¨
1
996.
[
[
2] Garrou, P. E. Chem Rev 1981, 81, 229–266.
L.; S e´ meril, D.; Bruneau, C.; Dixneuf, P. H. New J
Chem 2001, 25, 519–521; (b) C¸ etinkaya, B.; Demir,
S.; Ozdemir, I.; Toupet, L.; S e´ meril, D.; Bruneau, C.;
3] (a) Herrmann, W. A.; Weskamp, T.; B o¨ hm, V. P. W. Adv
Organomet Chem 2001, 48, 1–69; (b) Herrmann, W.
A.; K o¨ cher, C. Angew Chem, Int Ed 1997, 36, 2162–
¨
Dixneuf, P. H. Chem Eur J 2003, 9, 2323–2330.
¨
2
187.
[18] C¸ etinkaya, B.; Ozdemir, I., Bruneau, C.; Dixneuf, P.
[
[
4] Huang, J.; Schanz, H. J.; Stevens, E. D.; Nolan, S. P.
Organometallics 1999, 18, 2370–2375.
5] Schwarz, J.; B o¨ hm, V. P. W.; Gardiner, M. G.; Grosche,
M.; Herrmann, W. A.; Hieringer, W.; Raudaschl-
Sieber, G. Chem Eur J 2000, 6, 1773–1780.
H. J Mol Catal A 1997, 118, L1–L4.
¨
[19] Ozdemir, I.; Demir, S.; C¸ etinkaya, B. J Mol Catal A
2004, 215, 45–48.
[20] (a) G u¨ rb u¨ z, N.; Ozdemir, I.; Se c¸ kin, T.; C¸ etinkaya,
¨
B. J Inorg and Organomet Polym 2003, 14, 149–159;
¨
[
6] Hermann, W. A. Angew Chem, Int Ed 2002, 41, 1290–
(b) Ozdemir, I.; C¸ etinkaya, B.; Demir, S.; G u¨ rb u¨ z, N.
¨
1
309.
Catalysis Lett 2004, 97, 37–40; (c) Ozdemir, I.; Al1c1,
[
7] (a) Hermann, W. A.; Elison, M.; Fischer, J.; Kocher,
C.; Artus, G. R. J Chem Eur J 1996, 2, 772–780; (b)
Douthwaite, R. E.; Haussinger, D.; Green, M. L. H.;
Silcock, P. J.; Gomes, P. T.; Martins, A. M.; Danapou-
los, A. A. Organometallics 1999, 18, 4584–4590; (c)
Scholl, M.; Trnka, T. M.; Morgan, J. P.; Grubbs, R.
H. Tetrahedron Lett 1999, 40, 2247–2250; (d) Javar-
pour, L.; Nolan, S. P. Organometallics 2000, 19, 2055–
B.; G u¨ rb u¨ z, N.; C¸ etinkaya, E.; C¸ etinkaya, B. J Mol
Catal A 2004, 217, 37–40.
[21] Hill, J. E.; Nile, T. A. J Organomet Chem 1997, 137,
293–300.
[22] Chen, A. C.; Ren, L.; Decken, A.; Crudden, C. M.
Organometallics 2000, 19, 3459–3461.
[23] Sakai, M.; Ueda, M.; Miyaura, N. Angew Chem, Int
Ed 1998, 37, 3279–3281.
2
057.
[24] F u¨ rstner, A.; Krause, H. Adv Synth Catal 2001, 343,
343–350.
[25] (a) G u¨ rb u¨ z, A.; Ozdemir, I.; Demir, S.; C¸ etinkaya, B.
[
[
8] Poyatus, M.; Uriz, P.; Mata, J. A.; Claver, C.;
Fernandez, E.; Peris, E. Organometallics 2003, 22,
¨
4
40–444.
J Mol Catal A 2004, 209, 23–28; (b) Arduengo, A. J.;
Krafczyk, R.; Schmutzler, R. Tetrahedron 1999, 55,
14523–14534.
9] (a) Gr u¨ ndemann, S.; Kovacevic, A.; Albrecht, M.;
Faller, J. W.; Crabtree, R. H. Chem Commun
2
001, 2274–2275; (b) Gr u¨ ndemann, S.; Albrecht, M.;
[26] Batey, R. A.; Thadani, A. N.; Smil, D. V. Org Lett 1999,
1, 1683–1686.
[27] Chatt, J.; Venanzi, L. M. J Chem Soc 1975, 4735–4736.
Kovacevic, A.; Faller, J. W.; Crabtree, R. H. J Chem
Soc, Dalton Trans 2002, 2163–2167.