5
Reactions; Wiley-VCH: Weinheim, 1998; (c) Miyaura, N. Cross-
Coupling Reaction; Springer: Berlin, 2002; (d) Negishi, E.
Handbook of Organopalladium Chemistry for Organic Synthesis;
Wiley-Interscience: New York, 2002; (e) de Meijere, A.;
Diederich, F. Metal-Catalyzed Cross-Coupling Reactions; Wiley-
VCH: Weinheim, 2004.
Advances. 2013, 3, 1317; (c) Kore, R.; Srivastava R. RSC
Advances. 2012, 2, 10072.
14. Collman, J. P.; Zhong, M. Org. Lett. 2000, 2, 1233.
15. Kyle, K. R.; Ryu, C. K.; DiBenedetto, J. A.; Ford, P. C. J. Am.
Chem. Soc. 1991, 113, 2954.
16. Braga, D.; Maini, L.; Mazzeo, P. P.; Ventura, B. Chem. Eur. J.
2010, 16, 1553.
5. (a) Hassan, J.; Sevignon M.; Gozzi, C.; Schulz, E.; Lemaire, M.
Chem. Rev. 2002, 102, 1359; (b) Beletskaya, I. P.; Cheprakov, A.
V. Coord Chem. ReV. 2004, 248, 2337; (c) Siemsen, P.;
Livingston, R. C.; Diederich, F. Angew. Chem., Int Ed. 2000, 39,
2632; (d) Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003,
42, 5400.
17. Yang, Y.C.; Ward, J.R.; Seiders, R.P. Inorg. Chem. 1985, 24,
1765.
18. Catalytic procedure: Sonogashira C-C coupling reaction: For the
reaction performed at standard condition, iodobenzene,
phenylacetylene, K2CO3, and catalyst were taken in Teflon-coated
stainless-steel autoclave, and the reaction was performed at 140 °C
for 12 h. For the reaction performed under N2 atmosphere,
autoclave was thoroughly flushed with N2 for 10 minutes and then
the reaction vessel was kept at 1 bar N2 pressure at ambient
temperature. Temperature of the autoclave was raised to 140 °C
and the reaction was carried for 12 h. Progress of the reaction was
analyzed by Gas-chromatograph (Younglin YL6100) and products
were identified by GC-MS (Shimadzu, QP2010 Ultra). After the
reaction, reaction mixture was filtered and evaporated. The crude
products were purified by column chromatography on silica gel
using hexane/ethyl acetate to afford the corresponding coupled
products.
6. (a) Saito, S.; Ohtani, S.; Miyaura, N. J. Org.Chem. 1997, 62,
8024; (b) Zim, D.; Lando, V. R.; Dupond, J.; Monteiro,A. L. Org.
Lett. 2001, 3, 3049; (c) Beletskaya, I. P.; Latyshev, G. V.;
Tsvetkov, A. V.; Lukashev, N. V. Tetrahedron Lett. 2003, 44,
5011; (d) Percec, V.; Golding, G. M.; Smidrkal, J.; Weichold, O.
J. Org. Chem. 2004, 69, 3447; (e) Wang, L.; Li, P.; Zhang, Y.
Chem. Commun. 2004, 514.
7. (a) Thathagar, M. B.; Beckers, J.; Rothenberg, G. J. Am.Chem.
Soc. 2002, 124, 11858; (b) Thathagar, M. B.; Beckers, J.;
Rothenberg, G. Adv. Synth. Catal. 2003, 345, 979.
8. (a) Okuro, K.; Furuune, M.; Enna, M.; Miura, M.; Nomura, M. J.
Org. Chem. 1993, 58, 4716; (b) Gujadhur, R. K.; Bates, C. G.;
Venkataraman, D. Org. Lett. 2001, 3, 4315; (c) Thathagar, M. B.;
Beckers, J.; Rothenberg, G. Green Chem. 2004, 6, 215; (d) Ma,
D.; Liu, F. Chem. Commun. 2004, 1934; (f) Saejueng, P.; Bates,
C. G.; Venkataraman, D. Synthesis. 2005, 1706.
C-C homo-coupling reaction: Phenylacetylene, triethylamine,
catalyst, and acetonitrile were taken in round bottom flask and the
reaction was performed under ambient condition. During the
reaction, O2 was bubbled through the reaction mixture. Progress of
the reaction was analyzed by Gas-chromatograph and product was
identified by GC-MS. After the reaction, reaction mixture was
filtered and evaporated. The crude products were purified by
column chromatography on silica gel using hexane/ethyl acetate.
C-N coupling reaction: Phenylboronic acid, amine, catalyst, and
methanol were taken in round bottom flask and the reaction was
performed at ambient condition under air. Progress of the reaction
was analyzed by Gas-chromatograph and products were identified
by GC-MS. After the reaction, reaction mixture was filtered and
evaporated. The crude products were purified by column
chromatography on silica gel using hexane/ethyl acetate.
9. Ullmann, F. Ber. Dtsch. Chem. Ges. 1903, 36, 2382..
10. (a) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am.
Chem. Soc. 2001, 123, 7727; (b) Carril, M.; SanMartin, R.;
Dominguez, E. Chem. Soc. Rev. 2008, 37, 639; (c) Monnier, F.;
Taillefer, M. Angew. Chem. Int. Ed. 2009, 48, 6954.
11. (a) Mansour, M.; Giacovazzi, R.; Ouali, A.; Taillefer, M.; Jutand,
A. Chem. Commun. 2008, 6051; (b) Franc, G.; Jutand, A. Dalton
−787
Trans. 2010, 39, 7873 5; (c) He ,C.; Zhang G.; Ke, J.; Zhang,
H.; Miller, J. T.; Kropf A. J.; Lei A.; J. Am. Chem. Soc. 2013, 135,
488.
12. Adimurthy, S., Malakar, C. C.; Beifuss, U. J. Org. Chem. 2009,
74, 5648.
13. (a) Kore, R.; Satpati, B.; Srivastava, R. Chem. Eur. J. 2011,17
14360; (b) Kore, R.; Sridharkrishna, R.; Srivastava, R. RSC
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