A new, magnetic, silica-based, palladium nanocatalyst has been synthesized and employed for the first time in the direct coupling of acyl chlorides with terminal alkynes to prepare a variety of ynones. The synthesized nanocomposite is an excellent heterogeneous catalyst for copper-free, phosphine-free, C-C bond formation through the Sonogashira reaction under aerobic conditions at room temperature without the use of any additives and inert conditions. The synthesized catalyst has been comprehensively characterized by various techniques, such as XRD, SEM, TEM, energy-dispersive X-ray spectroscopy, X-ray photoelectron spectroscopy, inductively coupled plasma, FTIR spectroscopy, vibrating sample magnetometry, and atomic absorption spectroscopy. This nanocatalyst can be magnetically recovered and reused in multiple runs without any noticeable loss in catalytic activity.

Biotechnology and Management of Bioresources Division The Energy and Resources Institute Darbari Seth Block IHC Complex Lodhi Road New Delhi 110003 India

Department of Chemistry University of Delhi 105 Block B 1st floor GCNC Delhi 110007 India

Regional Centre of Advanced Technologies and Materials Department of Physical Chemistry Faculty of Science Palacký University Šlechtitelů 27 783 71 Olomouc Czech Republic

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X.-F. Wu, H. Neumann, M. Beller, Chem. Soc. Rev. 2011, 40, 4986-5009;

H.-Y. Jang, M. J. Krische, Acc. Chem. Res. 2004, 37, 653-661;

V. Ritleng, C. Sirlin, M. Pfeffer, Chem. Rev. 2002, 102, 1731-1769;

A. H. Cherney, N. T. Kadunce, S. E. Reisman, Chem. Rev. 2015, 115, 9587-9652;

C.-J. Li, Chem. Rev. 2005, 105, 3095-3165.

J. Marco-Contelles, E. de Opazo, J. Org. Chem. 2002, 67, 3705-3717;

C. J. Forsyth, J. Xu, S. T. Nguyen, I. A. Samdal, L. R. Briggs, T. Rundberget, M. Sandvik, C. O. Miles, J. Am. Chem. Soc. 2006, 128, 15114-15116;

A. Arcadi, M. Aschi, F. Marinelli, M. Verdecchia, Tetrahedron 2008, 64, 5354-5361;

C. A. Quesnelle, P. Gill, M. Dodier, D. St-Laurent, M. Serrano-Wu, A. Marinier, A. Martel, C. E. Mazzucco, T. M. Sticle, J. F. Barrett, D. M. Vyas, B. N. Balasubramanian, Bioorg. Med. Chem. Lett. 2003, 13, 519-524.

A. Jeevanandam, K. Narkunan, Y.-C. Ling, J. Org. Chem. 2001, 66, 6014-6020;

A. V. Kel′in, V. Gevorgyan, J. Org. Chem. 2002, 67, 95-98.

H. Arzoumanian, M. Jean, D. Nuel, A. Cabrera, J. L. G. Gutierrez, N. Rosas, Organometallics 1995, 14, 5438-5441;

B. G. Van den Hoven, B. ElAli, H. Alper, J. Org. Chem. 2000, 65, 4131-4137;

V. Lellek, H.-J. Hansen, Helv. Chim. Acta 2001, 84, 3548-3580.

M. Hojo, K. Tomita, A. Hosomi, Tetrahedron Lett. 1993, 34, 485-488.

R. K. Dieter, K. Lu, J. Org. Chem. 2002, 67, 847-855.

D. B. Grotjahn, S. Van, D. Combs, D. A. Lev, C. Schneider, M. Rideout, C. Meyer, G. Hernandez, L. Mejorado, J. Org. Chem. 2002, 67, 9200-9209;

X. Wang, J. Tan, L. Zhang, Org. Lett. 2000, 2, 3107-3109.

A. V. Kel′in, A. W. Sromek, V. Gevorgyan, J. Am. Chem. Soc. 2001, 123, 2074-2075.

A. S. Karpov, T. J. J. Muller, Org. Lett. 2003, 5, 3451-3454;

M. C. Bagley, D. D. Hughes, P. H. Taylor, Synlett 2003, 0259-0261.

C. G. Savarin, J. A. Murry, P. G. Dormer, Org. Lett. 2002, 4, 2071-2074.

M. C. Bagley, D. D. Hughes, R. Lloyd, V. E. C. Powers, Tetrahedron Lett. 2001, 42, 6585-6588;

D. D. Hughes, M. C. Bagley, Synlett 2002, 1332-1334.

A. Arcadi, F. Marinelli, E. Rossi, Tetrahedron 1999, 55, 13233-13250.

R. Chinchilla, C. Najera, Chem. Rev. 2014, 114, 1783-1836;

E. Negishi, V. Bagheri, S. Chatterjee, F. T. Luo, J. A. Miller, A. T. Stoll, Tetrahedron Lett. 1983, 24, 5181-5184;

Handbook of Organopalladium Chemistry for Organic Synthesis (Eds.: E.-I. Negishi, A. de Meijere), Wiley, New York, 2002;

M. S. Mohamed Ahmed, A. Mori, Org. Lett. 2003, 5, 3057-3060.

Y. Tohda, K. Sonogashira, N. Hagihara, Synthesis 1977, 777-778;

D. A. Alonso, C. Najera, M. C. Pacheco, J. Org. Chem. 2004, 69, 1615-1619;

L. Chen, C. J. Li, Org. Lett. 2004, 6, 3151-3153;

R. J. Cox, D. J. Ritson, T. A. Dane, J. Berge, J. P. H. Charmant, A. Kantacha, Chem. Commun. 2005, 1037-1039.

E. Mohammadi, B. Movassagh, M. Navidi, Helv. Chim. Acta 2014, 97, 70-75;

W. Sun, Y. Wang, X. Wu, X. Yao, Green Chem. 2013, 15, 2356-2360;

W. Yin, H. He, Y. Zhang, D. Luo, H. He, Synthesis 2014, 46, 2617-2621.

H. Yuan, Y. Shen, S. Yu, L. Shan, Q. Sun, W. Zhang, Synth. Commun. 2013, 43, 2817-2823;

S. S. Palimkar, P. H. Kumar, N. R. Jogdand, T. Daniel, R. J. Lahoti, K. V. Srinivasan, Tetrahedron Lett. 2006, 47, 5527-5530;

C. Taylor, Y. Bolshan, Org. Lett. 2014, 16, 488-491.

R. Hudson, Y. Feng, R. S. Varma, A. Moores, Green Chem. 2014, 16, 4493-4505;

R. B. N. Baig, R. S. Varma, Chem. Commun. 2013, 49, 752-770;

M. B. Gawande, P. S. Branco, R. S. Varma, Chem. Soc. Rev. 2013, 42, 3371-3393;

V. Polshettiwar, R. S. Varma, Green Chem. 2010, 12, 743-754.

A. Keivanloo, M. Bakherad, B. Bahramian, S. Baratnia, Tetrahedron Lett. 2011, 52, 1498-1502;

M. Navidi, B. Movassagh, S. Rayati, Appl. Catal. A 2013, 452, 24-28;

M. Bakherad, A. Keivanloo, B. Bahramian, S. Jajarmi, Synlett 2011, 3, 311-314;

M. Genelot, V. Dufaud, L. Djakovitch, Adv. Synth. Catal. 2013, 355, 2604-2616;

S. Santra, K. Dhara, P. Ranjan, P. Bera, J. Dash, S. K. Mandal, Green Chem. 2011, 13, 3238-3247;

M. A. Bhosale, T. Sasakib, B. M. Bhanage, Catal. Sci. Technol. 2014, 4, 4274-4280.

M. B. Gawande, Y. Monga, R. Zboril, R. K. Sharma, Coord. Chem. Rev. 2015, 288, 118-143;

S. Zhou, M. Johnsona, J. G. C. Veinot, Chem. Commun. 2010, 46, 2411-2413;

G. A. Sotiriou, A. M. Hirt, P. Y. Lozach, A. Teleki, F. Krumeich, S. E. Pratsinis, Chem. Mater. 2011, 23, 1985-1992;

Y. Lien, T. M. Wu, J. Colloid Interface Sci. 2008, 326, 517-521;

Y. Lu, Y. Yin, B. T. Mayers, Y. Xia, Nano Lett. 2002, 2, 183-186;

S. Kralj, M. Drofenik, D. Makovec, J. Nanopart. Res. 2011, 13, 2829-2841.

R. K. Sharma, S. Sharma, S. Dutta, R. Zboril, M. B. Gawande, Green Chem. 2015, 17, 3207-3230;

S. C. Tsang, C. H. Yu, X. Gao, K. Tam, J. Phys. Chem. B 2006, 110, 16914-16922;

D. Niu, Y. Li, X. Qiao, L. Li, W. Zhao, H. Chen, Q. Zhao, Z. Mac, J. Shi, Chem. Commun. 2008, 4463-4465;

J. L. Vivero-Escoto, R. C. H. Phillips, W. Lin, Chem. Soc. Rev. 2012, 41, 2673-2685.

M. B. Gawande, A. Rathi, I. D. Nogueira, R. S. Varma, P. P. Branco, Green Chem. 2013, 15, 1895-1899;

R. K. Sharma, Y. Monga, A. Puri, G. Gaba, Green Chem. 2013, 15, 2800-2809;

M. B. Gawande, S. N. Shelke, R. Zboril, R. S. Varma, Acc. Chem. Res. 2014, 47, 1338-1348;

R. K. Sharma, M. Yadav, R. Gaur, Y. Monga, A. Adholeya, Catal. Sci. Technol. 2015, 5, 2728-2740;

R. K. Sharma, M. Yadav, Y. Monga, R. Gaur, A. Adholeya, R. Zboril, R. S. Varma, M. B. Gawande, ACS Sustainable Chem. Eng. 2016, 4, 1123-1130;

R. K. Sharma, R. Gaur, M. Yadav, A. K. Rathi, J. Pechousek, M. Petr, R. Zboril, M. B. Gawande, ChemCatChem 2015, 7, 3495-3502.

V. Polshettiwar, R. S. Varma, Org. Biomol. Chem. 2009, 7, 37-40.

Z. Zhang, F. Zhang, Q. Zhu, W. Zhao, B. Ma, Y. Ding, J. Colloid Interface Sci. 2011, 360, 189-194.

S. Wang, Z. Zhang, B. Li, J. Li, Catal. Sci. Technol. 2013, 3, 2104-2112;

J. Wang, S. Zheng, Y. Shao, J. Liu, Z. Xu, D. Zhu, J. Colloid Interface Sci. 2010, 349, 293-299.

R. Abu-Reziq, H. Alper, Appl. Sci. 2012, 2, 260-276;

R. Abu-Reziq, H. Alper, D. S. Wang, M. L. Post, J. Am. Chem. Soc. 2006, 128, 5279-5282;

Q. Zhang, H. Su, J. Luo, Y. Wei, Green Chem. 2012, 14, 201-208.

G. Kumar, J. R. Blackburn, R. G. Albrtdge, W. E. Moddeman, M. M. Jones, Inorg. Chem. 1972, 11, 296-300.

J. Zhu, J. He, X. Du, R. Lu, L. Huang, X. Ge, Appl. Surf. Sci. 2011, 257, 9056-9062;

M. Kooti, M. Afshari, Mater. Res. Bull. 2012, 47, 3473-3478;

M. Yamaura, R. L. Camilo, L. C. Sampaio, M. A. Macedo, M. Nakamurad, H. E. Toma, J. Magn. Magn. Mater. 2004, 279, 210-217;

M. Masteri-Farahani, N. Tayyebi, J. Mol. Catal. A: Chem. 2011, 348, 83-87;

M. Esmaeilpour, A. R. Sardariana, J. Javidi, Appl. Catal. A 2012, 445-446, 359-367.

A. Hu, G. T. Yes, W. Lin, J. Am. Chem. Soc. 2005, 127, 12486-12487;

R. G. Digigowa, J.-F. Dechézelles, H. Dietsch, I. Geissbühler, D. Vanhecke, C. Geers, A. M. Hirt, B. R. Rutishauser, A. P. Fink, J. Magn. Magn. Mater. 2014, 362, 72-79.

H. Plenio, Angew. Chem. Int. Ed. 2008, 47, 6954-6956;

Angew. Chem. 2008, 120, 7060-7063;

A. Tougerti, S. Negri, A. Jutand, Chem. Eur. J. 2007, 13, 666-676;

H. Lu, L. Wang, F. Yang, R. Wua, W. Shen, RSC Adv. 2014, 4, 30447-30452.

An efficient copper-based magnetic nanocatalyst for the fixation of carbon dioxide at atmospheric pressure