Sonogashira Couplings of Aryl Bromides: Room Temperature, Water Only, No Copper
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1 Sonogashira Couplings of Aryl omides: Room Temperature, Water nly, o Copper uce. Lipshutz, David W. Chung, and ian Rich rg.lett. ASAP Article Presentation By ora Jameson Current Lit 08/30/2008 ora Wipf Group Page 1 of 11 9/7/2008 1
2 Sonogashira Coupling: Possible Catalytic Cycle Seminal Publications: K. Sonogashira, Y. Tohda,. agihara. Tetrahedron Letters (50): Andrew G. Myers and Peter S. Dragovich rg. Synth 1998 Coll. Vol. 9: 117 ora Wipf Group Page 2 of 11 9/7/2008 2
3 Sonogashira Coupling as a Tool in rganic Synthesis A. S. Karpov, T. J. J. Müller, Synthesis, 2003, SiMe 3 SiMe 3 Pd(PP 3 ) 2 Cl 2 / CuI benzene / Et 3 90C / 2d S. Liu, C. Michel, M. Schmittel, rg. Lett., 2000, 2(25); I MM PPh 3, PdCl 2 (PPh 3 ) 2 MM Et 3, CuI K. Y. Tsang, M. A. imble, J. B. emmer, rg. Lett., 2003, 5(23); ora Wipf Group Page 3 of 11 9/7/2008 3
4 o Copper Sonogashira Couplings A. R. Gholap, K. Venkatesan, R. Pasricha, T. Daniel, R. J. Lahoti, K. V. Srinivasan, J. rg. Chem., 2005, 70, C. Yi, R. ua, J. rg. Chem., 2006, 71, Y. Liang, Y.-X. Xie, J.-. Li, J. rg. Chem., 2006, 71, ora Wipf Group Page 4 of 11 9/7/2008 4
5 Aqueous Cross-Coupling X2 R I [Pd]/Et 3 C 3 C/ 2, R.T. R R C. Li, D. Chen, C. W. Costello, rg. Proc. Res. Dev., 1997, 1 (4), X ArB() 2 Pd/C, K 2 C 3 2, R.T., 12h Ar. Sakurai, T. Tsukuda, T. irao, J. rg. Chem., 2002, 67(8); A. Bino, M. Ardon, and E. Shirman, Science, 8 April : ora Wipf Group Page 5 of 11 9/7/2008 5
6 Micellar Catalysis J.. M. eijnen, V. G. de uijn, L. J. P. van den oeke and J. T. F. Keurentjes Chem. Engineering and Processing Vol. 42, 3, 2003, Pages perfluorooctanoic acid D. C. Berndt, M. E. Ayoub, M.. Akhavan-Tafti, Int. J. of Chem. Kinetics, Vol 19, 6, 1987, Triton -X100 ij 30 ora Wipf Group Page 6 of 11 9/7/2008 6
7 Aqueous Mediated Coupling The use of PTS: micellar catalyst PTS (n = ca. 13) ( 2 ) 2 B Pd(dtbpf)Cl 2, Et 3 2% wt PTS, rt, 5h Lipshutz, B.. et al. rg. Lett. 2008, 10, Bn I Pd(dtbpf)Cl 2, Et 3 Bn Bn Ts TBS 15% wt PTS, rt Bn Ts TBS Lipshutz, B..; Taft, B. R. rg. Lett. 2008, 10, ora Wipf Group Page 7 of 11 9/7/2008 7
8 Title Paper Sonogashira Couplings of Aryl omides: Room Temperature, Water nly, o Copper Unprecedented Sonogashira cross-coupling in water at ambient temperatures Absence of both copper and organic solvent Use of commercially available reagents ora Wipf Group Page 8 of 11 9/7/2008 8
9 Ligand Studies P(Cy) 2 Fe P(tBu) 2 PdCl 2 P(tBu) 2 Pd Cl Me P(Cy) 2 Me P(Cy) 2 X-Phos Pd(dtbpf)Cl 2 eolyst TM CX31 (Cy-vBRIDP) R = Cy (Cy-cBRIDP) R - tbu (cbridp) degassed solvents used for X-Phos, obtained best results with commercially available ligand and catalyst using catalyst 6 obtained similar results using degassed or nondegassed solvent 1% PdCl 2 (C 3 C) 2, X-Phos R' R R' Cs 2 C 3, 3%PTS, 2, rt R Suzuki, K.; Fontaine, A.; ori, Y.; Kobayashi, T. Synlett 2007, ora Wipf Group Page 9 of 11 9/7/2008 9
10 Reaction Scope Ar- alkyne base time product yield Ph Cs 2 C 3 20h 99% Ph 2 C n C n Et 3 18h 2 99% Et 3 21h 98% (C 2 ) 4 Cl (C 2 ) 4 Cl (n-bu) 3 c 23h 0% (n-ct) 3 c 23h 0% Using PdCl2(C3C)2 + Ligand 1 in 3% PTS/2 at rt ora Wipf Group Page 10 of 11 9/7/
11 Conclusions Cl Cl (C 2 ) 9-3% Pd(Ac) 2, 6% ligand 6 6% PTS/ 2, Et 3, rt, 6h Cl Cl (C 2 ) 9 - Aryl bromide Sonogashira Coupling in aqueous solvent Absence of copper and organic solvents Reactions at ambient temperatures Use of PTS as micellar catalyst Possible applications in industrial chemistry ora Wipf Group Page 11 of 11 9/7/
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