(NHC)-Pd(II) complexes with hydrophilic nitrogen ligands: catalytic properties in neat water
The cleavage reactions of the dimers [(NHC)PdX2]2 with hydrophilic N-donors, L, afforded the mixed-ligand complexes of the type trans-[(NHC)LPdX2] (X = Cl or Br; NHC = 1,3-dialkylbenzimidazol-2-ylidene (BIm) or bis(imino)acenaphthene-annulated bis(2,6-diisopropylphenyl)imidazol-2-ylidene (BIAN-IPr); L = diethanolamine (DEA), morpholine (MOR), and 3-pyridinecarboxylic acid (3-PCA)). The new complexes (1--3) were characterized by elemental analysis and spectroscopic methods and the molecular structure of 1a was determined by X-ray diffraction studies. These complexes were applied in the Suzuki--Miyaura cross-coupling reaction of phenylboronic acid with aryl halides in neat water. The activities of catalysts were monitored by gas chromatography--flame ionization detector and nuclear magnetic resonance. Whereas the complexes with DEA or 3-PCA ligands did not show significant difference in the activity, the BIAN-IPr complexes 1b and 3b bearing DEA and 3-PCA, displayed the highest catalytic activity at 100 °C.
(NHC)-Pd(II) complexes with hydrophilic nitrogen ligands: catalytic properties in neat water
The cleavage reactions of the dimers [(NHC)PdX2]2 with hydrophilic N-donors, L, afforded the mixed-ligand complexes of the type trans-[(NHC)LPdX2] (X = Cl or Br; NHC = 1,3-dialkylbenzimidazol-2-ylidene (BIm) or bis(imino)acenaphthene-annulated bis(2,6-diisopropylphenyl)imidazol-2-ylidene (BIAN-IPr); L = diethanolamine (DEA), morpholine (MOR), and 3-pyridinecarboxylic acid (3-PCA)). The new complexes (1--3) were characterized by elemental analysis and spectroscopic methods and the molecular structure of 1a was determined by X-ray diffraction studies. These complexes were applied in the Suzuki--Miyaura cross-coupling reaction of phenylboronic acid with aryl halides in neat water. The activities of catalysts were monitored by gas chromatography--flame ionization detector and nuclear magnetic resonance. Whereas the complexes with DEA or 3-PCA ligands did not show significant difference in the activity, the BIAN-IPr complexes 1b and 3b bearing DEA and 3-PCA, displayed the highest catalytic activity at 100 °C.
___
- (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457–2483; (b) Stanforth, S. P. Tetrahedron 1998, 54, 263–303; (c) Suzuki, A. J. Organomet. Chem. 1999, 576, 147–168; (d) Guerret, D. O.; Gabba F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39–92; (e) Suzuki, A. J. Organomet. Chem. 2002, 653, 83–90; (f) Herrmann, W. A. Angew. Chem. Int. Ed. 2002, 41, 1290–1309; (g) Crudden, C. M.; Allen, D. P. Coord. Chem. Rev. 2004, 248, 2247–2273.
- (a) Bedford, R. B.; Cazin, C. S. J.; Holder, D. Coord. Chem. Rev. 2004, 248, 2283–2321; (b) Viciu, M. S.; Nolan, S. P. Top. Organomet. Chem. 2005, 14, 241–278; (c) Martin, R.; Buchwald, S. L. Acc. Chem. Res. 2008, 41, 1461–1473; (d) Kantchev, A. B.; O’Brien, C. J.; Organ, M. G. Angew. Chem. Int. Ed. 2007, 46, 2768–2813; (e) Hahn, F. E.; Jahnke, M. C. Angew. Chem. Int. Ed. 2008, 47, 3122–3172.
- (a) Cornils, B.; Herrmann, W. A. Applied Homogeneous Catalysis with Organometallic Compounds Vols. 1 and 2 ; VCH: New York, 1996; (b) Dieldrich, F.; Stang, P. J. Metal-Catalyzed Cross-Coupling Reactions; Wiley-VCH, Weinheim, 1998; (c) Miyaura, N. Cross-Coupling Reactions; Springer: Berlin, 2002; (d) Phan, N. T. S.; van der Sluy, M.; Jones, C. W. Adv. Synth. Catal. 2006, 348, 609–679.
- Alcarazo, M.; Stork, T.; Anoop, A.; Thiel, W.; F¨ urstner, A. Angew. Chem. Int. Ed. 2010, 49, 2542-2546.
- (a) O’Brien, C. J.; Kantchev, E. A. B.; Valente, C.; Hadei, N.; Chass, G. A.; Lough, A.; Hopkinson, A. C.; Organ, M. G. Chem. Eur. J. 2006, 12, 4743–4748; (b) Organ, M. G.; Chass, G. A.; Fang, D. C.; Hopkinson, A. C.; Valente, C. Synthesis 2008, 2776–2797; (c) Chen, M. T.; Vicic, D. A.; Turner, M. L.; Navarro, O. Organometallics 2011, 30, 5052–5056; (d) Chen, M. T.; Vicic, D. A.; Turner, M. L.; Navarro, O. Organometallics 2011, 30, 6770–6773. C ¸ alimsiz, S.; Organ, M. G. Chem. Commun. 2011, 47, 5181–5183.
- (a) Shaughnessy, K. H. Chem. Rev. 2009, 109, 643–710; (b) Pinault, N.; Bruce, D. W. Coord. Chem. Rev. 2003, 241, 1-25; (c) Schaper, L. A.; Hock, S. J.; Herrmann, W. A.; Kuhn, F. E. Angew. Chem. Int. Ed. 2013, 51, 2-22; (d) Velazquez, H. D.; Verpoort, F. Chem. Soc. Rev. 2012 41, 7032-7060.
- (a) Moore, L. R.; Western, E. C.; Craciun, R.; Spruell, J. M.; Dixon, D. A.; O’Halloran, K. P.; Shaughnessy, K. H. Organometallics 2008, 27, 576-593; (b) T¨ urkmen, H.; Pelit, L.; C ¸ etinkaya, B. J. Mol. Cat. A. 2011, 348, 88–93. (a) Fleckenstein, C.; Roy, S.; Leuth¨ außer, S.; Plenio, H. Chem. Commun. 2007, 2870–2872; (b) Roy, S.; Plenio, H. Adv. Synth. Catal. 2010, 352, 1014–1022; (c) Li, L.; Wang, J.; Zhou, C.; Wang, R.; Hong, M. Green Chem. 2011, 13, 2071–2077; (d) Tau, T.; Feng, X.; Wang, Z.; Liu, X. Dalton Trans. 2010, 10598–10600; (e) Karimi, B.; Akhavan, P. F. Chem. Commun. 2011, 47, 7686–7688; (f) G¨ ulcemal, S.; Kahraman, S.; Daran, J. C.; C ¸ etinkaya, E.; C ¸ etinkaya, B. J. Organomet. Chem. 2010, 694, 3580–3589; (g) ¨ Ozdemir, ˙I.; Yi˘ git, B.; C ¸ etinkaya, B.; ¨ Ulk¨ u, D.; Tahir, M. N.; Arıcı, C. J. Organomet. Chem. 2001, 633, 27–32; (h) Liu, N.; Jin, Z. Green Chem. 2012, 14, 592–597; (i) Wang, W.; Wu, J.; Xia, C.; Li, F. Green Chem. 2011, 13, 3440–7044.
- T¨ urkmen, H.; Can, R.; C ¸ etinkaya, B. Dalton Trans. 2009, 7039–7044.
- Fantasia, S.; Petersen, J. L.; Jacobsen, H.; Cavallo, L.; Nolan, S. P. Organometallics 2007, 26, 5880–5889.
- Diebolt, O.; Jurcik, V.; Costa, R. C.; Braunstein, P.; Cavallo, L.; Nolan, S. P.; Slawin, A. M. Z.; Cazin, C. S. J. Organometallics 2010, 29, 1443–1450.
- (a) Dastgir, S.; Coleman, K. S.; Cowley, A. R.; Green, C. L. H. Dalton Trans. 2009, 7203–7214; (b) Vasudevan, K. V.; Butorac, R. R.; Abernethy, C. D.; Cowley, A. H. Dalton Trans. 2010, 39, 7401–7408; (c) Tu, T.; Fang, W.; Jiang, J. Chem. Commun. 2011, 47, 12358–12360; (d) Tu, T.; Fang, W.; Xu, M.; Zhou, Y. Org. Lett. 2012, 14, 4250–1253; (e) Merino, E.; Poli, E.; Diaz, U.; Brunel, D. Dalton Trans. 2012, 10913–10918.
- T¨ urkmen, H.; S ¸ahin, O.; B¨ uy¨ ukg¨ ung¨ or, O.; C ¸ etinkaya, B. Eur. J. Inorg. Chem. 2006, 4915–4921.
- T¨ urkmen, H.; Pape, T.; Hahn, F. E.; C ¸ etinkaya, B. Eur. J. Inorg. Chem. 2009, 285–294.
- Bruker. SMART ; Bruker AXS, 2000.
- Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467–473.
- Sheldrick, G. M. SHELXL-97 ; Universitat G¨ ottingen 1997.
- Spek, A. L. PLATON - A Multipurpose Crystallographic Tool ; Utrecht University, the Netherlands, 2005.
- G¨ ok¸ ce, A. G.; T¨ urkmen, H.; Ayg¨ un, M.; C ¸ etinkaya, B.; B¨ uy¨ ukg¨ ung¨ or, O. Struct. Chem. 2008, 19, 57–62.
- G¨ ok¸ ce, A. G.; T¨ urkmen, H.; Ayg¨ un, M.; C ¸ etinkaya, B.; Kazak, C. Acta Cryst. 2004, C60, m254–m255.
- Marion, N.; Navarro, O.; Mei, J.; Stevens, E. D.; Scott, N. M.; Nolan, S. P. J. Am. Chem. Soc. 2006, 128, 4101–4111.
- Liu, Q. X.; Song, H. B.; Xu, F. B.; Li, Q. S.; Zeng, X.; Leng, X. B.; Zhang, Z. Z. Polyhedron 2003, 2, 1515–1521. Petrovic, Z. D.; Djuran, M. I.; Heinemann, F. M.; Rajkovic, S.; Trifunovic, S. R. Bioorg. Chem. 2006, 34, 225–234. (a) Flemming J. P.; Pilon, M. C.; Borbulevitch, O. Y.; Antipin M. Y.; Grushin, V. V. Inorg. Chim. Acta 1998, 280, 87–98; (b) Ravi, K.; Maverick, A. V.; Fronczek, F. R. Acta Cryst. 1993, C49, 1766–1767; (c) Lippard, S. J.; Morehouse, S. M. J. Am. Chem. Soc. 1969, 91, 2504–2509; (d) Chen, M. T.; Vicic, D. A.; Turner, M. L.; Navarro, O. Organometallics 2011, 30, 5052–5056.
- Letsinger, R. L.; Skoog, I. J. Am. Chem. Soc. 1955, 77, 2491–2494.