Abstract
The immobilisation of an oxime-based palladacycle on polyvinylpyridine (PVP) resin affords a reusable, air, moisture and thermally stable palladium precatalyst which exerts high activity in Suzuki-Miyaura reactions both in batch as well as continuous-flow processes. Evidence is presented which shows that, besides serving as an anchor for the precatalyst, PVP also acts as a scavenger for Pd particles present in solution.
Key words
continuous-flow process - heterogeneous catalysis - homogeneous catalysis - microreactor - microwave - palladium - Suzuki-Miyaura reaction
References
1 Schwartz J.
Acc. Chem. Res.
1985,
18:
302
2 Garrett CE.
Prasad K.
Adv. Synth. Catal.
2004,
346:
889
3a Immobilized Catalysts , In Topics in Current Chem istry
Vol. 242:
Kirschning A.
Springer;
Berlin:
2004.
3b Solodenko W.
Frenzel T.
Kirschning A. In
Polymeric Materials in Organic Synthesis and Catalysis
Buchmeiser MR.
Wiley-VCH;
Weinheim:
2003.
3c McNamara CA.
Dixon MJ.
Bradley M.
Chem. Rev.
2002,
102:
3275
4 Dai L.-X.
Angew. Chem. Int. Ed.
2004,
43:
5726
5 Ramarao C.
Ley SV.
Smith SC.
Shirley IM.
DeAlmeida N.
Chem. Commun.
2002,
1132
6 Ley SV.
Mitchell C.
Pears D.
Ramarao C.
Yu JQ.
Zhou WZ.
Org. Lett.
2003,
5:
4665
7 Kobayashi S.
Akiyama R.
Chem. Commun.
2003,
449
8 Akiyama R.
Kobayashi S.
J. Am. Chem. Soc.
2003,
125:
3412
9 Okamoto K.
Akiyama R.
Kobayashi S.
Org. Lett.
2004,
6:
1987
10 Trost BM.
Keinan E.
J. Am. Chem. Soc.
1978,
100:
7779
11 Datta A.
Ebert K.
Plenio H.
Organometallics
2003,
22:
4685
12 Yamada YMA.
Takeda K.
Takahashi H.
Ikegami S.
J. Org. Chem.
2003,
68:
7733
13 Kunz U.
Leue S.
Stuhlmann F.
Sourkouni-Argirusi G.
Wen H.
Jas G.
Kirschning A.
Eur. J. Org. Chem.
2004,
3601
14 Vassylyev O.
Chen J.
Panarello AP.
Khinast JG.
Tetrahedron Lett.
2005,
46:
6865
15 Smith MD.
Stephan AF.
Ramarao C.
Brennan PE.
Ley SV.
Chem. Commun.
2003,
2652
16 Crudden CM.
Sateesh M.
Lewis R.
J. Am. Chem. Soc.
2005,
127:
10045
17a Prockl SS.
Kleist W.
Gruber MA.
Köhler K.
Angew. Chem. Int. Ed.
2004,
43:
1881
17b Conlon DA.
Pipik B.
Ferdinand S.
LeBlond CR.
Sowa JR.
Izzo B.
Collins P.
Ho GJ.
Williams JM.
Shi YJ.
Sun YK.
Adv. Synth. Catal.
2003,
345:
931
18 Davies IW.
Matty L.
Highes DL.
Reiser PJ.
J. Am. Chem. Soc.
2001,
123:
10139
19 Yu K.
Sommer W.
Richardson JM.
Weck M.
Jones CW.
Adv. Synth. Catal.
2005,
347:
161
20 Bergbreiter DE.
Osburn PL.
Frels JD.
Adv. Synth. Catal.
2005,
347:
172
21 Biffis A.
Zecca M.
Basato M.
Eur. J. Inorg. Chem.
2001,
1131
22a Na Y.
Park S.
Han SB.
Han H.
Ko S.
Chang S.
J. Am. Chem. Soc.
2004,
126:
250
22b Jaska CA.
Manners I.
J. Am. Chem. Soc.
2004,
126:
9776
23 Andrews SP.
Stephan AF.
Tanaka H.
Ley SV.
Smith MD.
Adv. Synth. Catal.
2005,
347:
647
24 Mennecke K.
Grela K.
Kunz U.
Kirschning A.
Synlett
2005,
2948
25 Jas G.
Kirschning A.
Chem. Eur. J.
2003,
9:
5708
26a Kunz U.
Kirschning A.
Altwicker C.
Solodenko W.
J. Chromatogr., A
2003,
1006:
241
26b Kunz U.
Kirschning A.
Wen H.-L.
Solodenko W.
Cecillia R.
Kappe CO.
Turek T.
Catal. Today
2005,
105:
318
26c Kunz U.
Schönfeld H.
Solodenko W.
Jas G.
Kirschning A.
Ind. Eng. Chem. Res.
2005,
44:
8458
27 Alonso DA.
Nájera C.
Pacheco MC.
Org. Lett.
2000,
2:
1823
28a Dupont J.
Consorti CS.
Spencer J.
Chem. Rev.
2005,
105:
2527
28b Alonso DA.
Botella L.
Najéra C.
Pacheco MC.
Synthesis
2004,
1713
29 Ryabov AD.
Kazankov GM.
Yatsimirsky AK.
Kuz’mina LG.
Burtseva OY.
Dvortsova NV.
Polyakov VA.
Inorg. Chem.
1992,
31:
3083
30 Kirschning A.
Altwicker C.
Dräger G.
Harders J.
Hoffmann N.
Hoffmann U.
Schönfeld H.
Solodenko W.
Kunz U.
Angew. Chem. Int. Ed.
2001,
40:
3995
31 Davies HM.
Waji AM.
Org. Lett.
2005,
7:
2941
32 From in industrial point of view, it is commonly advantageous to promote continuous addition of reactants to an immobilised catalyst compared to repeatedly carrying out batch-wise procedures with the same catalyst. Indeed, each reisolation of the catalysts exerts stress on it which leads to reduced performance in the next run.
33 Moreno-Manas M.
Perez M.
Pleixats R.
J. Org. Chem.
1996,
61:
2346
34 Nowotny W.
Hanefeld U.
Van Koningsveld H.
Maschmeyer M.
Chem. Commun.
2000,
1877
35 de Vries AHM.
Mulders JMCA.
Mommers JHM.
Henderickx HJW.
de Vries JG.
Org. Lett.
2003,
5:
3285
36a Yu K.
Sommer W.
Richardson JM.
Weck M.
Jones CW.
Adv. Synth. Catal.
2005,
347:
161
36b Bergbreiter DE.
Osburn PL.
Frels JD.
Adv. Synth. Catal.
2005,
347:
172
37 Howard GA.
Khdary NH.
Analyst
2005,
130:
1432
38 Pugin B.
J. Mol. Cat. A: Chem.
1996,
107:
273
39 Solodenko W.
Kunz U.
Kirschning A.
Bioorg. Med. Chem. Lett.
2002,
12:
1833
40 Wright SW.
Hageman DL.
McClure LD.
J. Org. Chem.
1994,
59:
6095
41 Amatore C.
Jutand A.
Acc. Chem. Res.
2000,
33:
314
42 Part of this work was presented at the 8th International Symposium on Solid-Phase Synthesis & Combinatorial Libraries, 2-6 September, 2003, at Imperial College London, UK.
43 Xiong Z.
Wang N.
Dai M.
Li M.
Chen J.
Yang Z.
Org. Lett.
2004,
6:
3337
44 Badone D.
Baroni M.
Cardamone R.
Ielmini A.
Guzzi U.
J. Org. Chem.
1997,
62:
7170
45 Farina V.
Krishnan B.
Marshall DR.
Roth GP.
J. Org. Chem.
1993,
58:
5434
46 Byron DJ.
Gray GW.
Wilson RC.
J. Chem. Soc. C.
1966,
840
47 Williams HWR.
Eichler E.
Randall W.
Rooney CS.
Cragoe EJ.
J. Med. Chem.
1983,
26:
1196
48 Kon GAR.
J. Chem. Soc.
1948,
224
49 Wolfe JP.
Singer RA.
Yang BH.
Buchwald SL.
J. Am. Chem. Soc.
1999,
121:
9550
50 Takashi M.
Yoshiaki S.
Masami S.
Tsutomu F.
J. Org. Chem.
2005,
70:
2191
51 Hassanaly P.
Vernin G.
Dou HJM.
Metzger J.
Bull. Soc. Chim. Fr.
1976,
461
