A Phosphane-Free, Atom-Efficient Cross-Coupling Reaction of Triarylbismuths with Acyl Chlorides Catalyzed by MCM-41-Immobilized Palladium Complex

作者: Hong Zhao , Lin Yin , Mingzhong Cai

DOI: 10.1002/EJOC.201201432

关键词: Heterogeneous catalysisCoupling reactionPalladiumGreen chemistryChemistryYield (chemistry)CatalysisPolymer chemistryMCM-41Organic chemistryDenticity

摘要: The first phosphane-free, heterogeneous, atom-efficient cross-coupling reaction of triarylbismuths and acyl chlorides was achieved in N-methylpyrrolidone (NMP) with Bu3N as the base at 80 °C presence 1.5 mol-% MCM-41-immobilized bidentate nitrogen palladium complex [MCM-41–2N-Pd(OAc)2, MCM = mobile crystalline material] to yield a variety unsymmetrical biaryl ketones good excellent yields. This heterogeneous catalyst exhibited high activity, which similar that Pd(PPh3)4. can be recovered by simple filtration solution recycled least 10 consecutive trials without any decrease activity. Our system not only avoids use phosphane ligands, but also solves basic problem recovery reuse.

参考文章(112)
Derek H.R. Barton, Nubar Ozbalik, Manian Ramesh, The chemistry of orqanobismuth reagents: Part XIII ligand coupling induced by Pd(O) Tetrahedron. ,vol. 44, pp. 5661- 5668 ,(1988) , 10.1016/S0040-4020(01)81427-7
Pei-Wei Wang, Marye Anne Fox, A Polymer-Bound Bidentate-Phosphine-Palladium Complex as a Catalyst in the Heck Arylation Journal of Organic Chemistry. ,vol. 59, pp. 5358- 5364 ,(1994) , 10.1021/JO00097A043
Perumal Rajakumar, Muthialu Srisailas, Synthesis of chiral cyclophanes based on meta-terphenyl and pyridyl blocks Tetrahedron. ,vol. 57, pp. 9749- 9754 ,(2001) , 10.1016/S0040-4020(01)00966-8
Christian P. Mehnert, David W. Weaver, Jackie Y. Ying, Heterogeneous Heck Catalysis with Palladium-Grafted Molecular Sieves Journal of the American Chemical Society. ,vol. 120, pp. 12289- 12296 ,(1998) , 10.1021/JA971637U
Kunquan Yu, William Sommer, John?M. Richardson, Marcus Weck, Christopher?W. Jones, Evidence that SCS Pincer Pd(II) Complexes are only Precatalysts in Heck Catalysis and the Implications for Catalyst Recovery and Reuse Advanced Synthesis & Catalysis. ,vol. 347, pp. 161- 171 ,(2005) , 10.1002/ADSC.200404264
Baijun Liu, Guibin Wang, Wei Hu, Yuhui Jin, Chunhai Chen, Zhenhua Jiang, Wanjin Zhang, Zhongwen Wu, Yen Wei, Poly(aryl ether ketone)s with (3‐methyl)phenyl and (3‐trifluoromethyl)phenyl side groups Journal of Polymer Science Part A. ,vol. 40, pp. 3392- 3398 ,(2002) , 10.1002/POLA.10434
Alois Fürstner, David Voigtländer, Wolfgang Schrader, Dirk Giebel, Manfred T. Reetz, A “Hard/Soft” Mismatch Enables Catalytic Friedel−Crafts Acylations Organic Letters. ,vol. 3, pp. 417- 420 ,(2001) , 10.1021/OL0069251
J. S. Beck, J. C. Vartuli, W. J. Roth, M. E. Leonowicz, C. T. Kresge, K. D. Schmitt, C. T. W. Chu, D. H. Olson, E. W. Sheppard, S. B. McCullen, J. B. Higgins, J. L. Schlenker, A new family of mesoporous molecular sieves prepared with liquid crystal templates Journal of the American Chemical Society. ,vol. 114, pp. 10834- 10843 ,(1992) , 10.1021/JA00053A020
Hengquan Yang, Gaoyong Zhang, Xinlin Hong, Yinyan Zhu, Dicyano-functionalized MCM-41 anchored-palladium complexes as recoverable catalysts for Heck reaction Journal of Molecular Catalysis A: Chemical. ,vol. 210, pp. 143- 148 ,(2004) , 10.1016/J.MOLCATA.2003.09.009
Stephen G. Davies, Dirk Pyatt, Colin Thomson, Synthesis of 6-substituted-3,4-dihydro-2H-1-benzopyran-2-ones(dihydrocoumarins) via palladium catalysed coupling reactions Journal of Organometallic Chemistry. ,vol. 387, pp. 381- 390 ,(1990) , 10.1016/0022-328X(90)87186-H