Subscribe to RSS
DOI: 10.1055/s-0030-1258349
A Simple, Efficient, and Recyclable Phosphine-Free Catalytic System for Carbonylative Suzuki Coupling Reaction of Aryl and Heteroaryl Iodides
Publication History
Publication Date:
03 December 2010 (online)

Abstract
The carbonylative Suzuki cross-coupling reaction of arylboronic acid with aryl and heteroaryl iodides using polymer supported palladium-N-heterocyclic carbene complex (PS-Pd-NHC) as an efficient heterogeneous, recyclable catalyst is described. The developed catalytic system is found to be effective for the carbonylative coupling reaction of aryl, heteroaryl, and bicyclic heteroaryl iodides (5-iodoindole and 3-iodoquinoline) with various arylboronic acid derivatives providing good to excellent yields of the desired products. The protocol is advantageous due to the ease in handling of the catalyst and simple workup procedure, and environmentally benign with effective catalyst recyclability.
Key words
biaryl ketones - boron - heterogeneous catalysis - palladium - Suzuki carbonylation
- 1
The
Merck Index
11th ed.:
Budavari S. Merck; Rahway: 1989. - 2a
Fürstner A.Voigtländer D.Schrader W.Giebel D.Reetz MT. Org. Lett. 2001, 3: 417Reference Ris Wihthout Link - 2b
Song CE.Shim WH.Roh EJ.Choi JH. Chem. Commun. 2000, 1695Reference Ris Wihthout Link - 2c
Fillion E.Fishlock D.Wilsily A.Goll JM. J. Org. Chem. 2005, 70: 1316Reference Ris Wihthout Link - 3a
Bonnaire S.Carpentier JF.Mortreux A.Castanet Y. Tetrahedron Lett. 2001, 42: 3689Reference Ris Wihthout Link - 3b
Bonnaire S.Carpentier JF.Mortreux A.Castanet Y. Tetrahedron 2003, 59: 2793Reference Ris Wihthout Link - 4
Ishiyama T.Kizaki H.Hayashi T.Suzuki A.Miyaura N. J. Org. Chem. 1998, 63: 4726 - 5
Maerten E.Hassouna F.Bonnaire S.Mortreux A.Carpentier JF.Castanet Y. Synlett 2003, 1874 - 6
Andrus MB.Ma Y.Zang Y.Song C. Tetrahedron Lett. 2002, 43: 9137Reference Ris Wihthout Link - 7
Cai M.Zheng G.Zha L.Peng J. Eur. J. Org. Chem. 2009, 1585 - 8
Mingji D.Liang B.Wang C.You Z.Xiang J.Dong G.Chen J.Yang Z. Adv. Synth. Catal. 2004, 346: 1669 - 9
Neumann H.Brennfhrer A.Beller M. Adv. Synth. Catal. 2008, 350: 2437 - 10
Petz A.Peczely G.Pinter Z.Kollar L. J. Mol. Catal. A: Chem. 2006, 255: 97 - 11a
Ofele K. J. Organomet. Chem. 1968, 12: 42Reference Ris Wihthout Link - 11b
Wanzlick HJ.Schönherr HJ. Angew. Chem. Int. Ed. 1968, 7: 141Reference Ris Wihthout Link - 11c
Herrmann WA. Angew. Chem. Int. Ed. 2002, 41: 1290Reference Ris Wihthout Link - 12a
Weskamp T.Kohl FJ.Hieringer W.Gleich D.Herrmann WA. Angew. Chem. Int. Ed. 1999, 38: 2416Reference Ris Wihthout Link - 12b
Schwarz J.Biihm VPW.Gardiner MG.Grosche M.Herrmann WA.Hieringer W.Raudaschl-Sieber G. Chem. Eur. J. 2000, 6: 1773Reference Ris Wihthout Link - 13a
Byun JW.Lee YS. Tetrahedron Lett. 2004, 45: 1837Reference Ris Wihthout Link - 13b
Kim JW.Kim JH.Lee DH.Lee YS. Tetrahedron Lett. 2006, 47: 4745Reference Ris Wihthout Link - 13c
Tandukar S.Sen A. J. Mol. Catal., A: Chem. 2007, 268: 112Reference Ris Wihthout Link - 13d
Gomann A.Deverell JA.Munting KF.Jones RC.Rodemann T.Canty AJ.Smith JA.Guijt RM. Tetrahedron 2009, 65: 1450Reference Ris Wihthout Link - 14a
Tambade PJ.Patil YP.Bhanage BM. Appl. Organomet. Chem. 2009, 23: 235Reference Ris Wihthout Link - 14b
Tambade PJ.Patil YP.Bhanushali MJ.Bhanage BM. Synthesis 2008, 2347Reference Ris Wihthout Link - 14c
Tambade PJ.Patil YP.Bhanushali MJ.Bhanage BM. Tetrahedron Lett. 2008, 49: 2221Reference Ris Wihthout Link - 14d
Tambade PJ.Patil YP.Panda AG.Bhanage BM. Eur. J. Org. Chem. 2009, 3022Reference Ris Wihthout Link - 15a
Lempers HEB.Sheldon RA. J. Catal. 1998, 175: 62Reference Ris Wihthout Link - 15b
Zhao H.Zheng G.Sheng S.Cai M. Catal. Commun. 2009, 11: 158Reference Ris Wihthout Link