Microwave assisted Pd(OAc)2-catalyzed chemoselective reduction of aryl α,β-unsaturated esters with triethylsilane
محورهای موضوعی : Iranian Journal of CatalysisYogesh Kumar 1 , Renuka Yadav 2 , Anshu Kumar Sinha 3 , Pooja Rawat 4 , Gyandshwar Kumar Rao 5 , Chandra Mohan Srivastava 6 , Nirmala Kumari Jangid 7 , Anamika Srivastava 8 , Manish Srivastava 9 , Varun Rawat 10
1 - Department of Applied Chemistry, Amity School of Applied Sciences, Amity University Haryana, Gurugram-122413 (Haryana), India.
2 - Department of Applied Chemistry, Amity School of Applied Sciences, Amity University Haryana, Gurugram-122413 (Haryana), India.
3 - Department of Applied Chemistry, Amity School of Applied Sciences, Amity University Haryana, Gurugram-122413 (Haryana), India.
4 - Department of Applied Chemistry, Amity School of Applied Sciences, Amity University Haryana, Gurugram-122413 (Haryana), India.
5 - Department of Applied Chemistry, Amity School of Applied Sciences, Amity University Haryana, Gurugram-122413 (Haryana), India.
6 - Centre for Polymer Technology, Amity School of Applied Sciences, Amity University Haryana, Gurugram-122413 (Haryana), India.
7 - Department of Chemistry, Banasthali Vidyapith, Banasthali-304022 (Rajasthan), India.
8 - Department of Chemistry, Banasthali Vidyapith, Banasthali-304022 (Rajasthan), India.
9 - Department of Chemistry, Banasthali Vidyapith, Banasthali-304022 (Rajasthan), India.
10 - Department of Applied Chemistry, Amity School of Applied Sciences, Amity University Haryana, Gurugram-122413 (Haryana), India.
کلید واژه: reduction, Microwave, Palladium, Chemoselective, Triethylsilane,
چکیده مقاله :
In this communication, we have reported that the Pd(OAc)2–Et3SiH-DMF system promotes the microwave-assisted chemoselective reduction of aryl α,β-unsaturated esters in good yields. The protocol affords a convenient reduction of aryl-conjugated double bonds even in presence of other functional groups like esters, phenols, and ethers.
[1] (a) C. O. Kappe, Angew. Chem. Int. Ed. 43 (2004) 6250-6284. (b) C. O. Kappe, D. Dallinger. Nat. Drug Disc. Rev. 5 (2006) 51-63. (c) V. Polshettiwar, R. S. Varma, Acc. Chem. Res. 41 (2008) 629-639. (d) A.K. Nagariya, A. K. Meena, A. K. Kiran, A. K. Yadav, U. S. Niranjan, A. K. Pathak, B. Singh, M. M. Rao, J. Pharm. Res. 3 (2010) 575-580. (e) M. A. Surati, S. Jauhari, K. R. Desai, Arch. Appl. Sci. Res. 4 (2012) 645-661.
[2] (a) H. U. Blaser, C. Malan, B. Pugin, F. Spindler, H. Steiner, M. Studer, Adv. Synth. Catal. 345 (2003) 103-151. (b) R. Noyori, M. Kitamura, T.Ohkuma, Proc. Natl. Acad. Sci. USA 101 (2004) 5356-5362. (c) M. Hudlicky, Reductions in Organic Chemistry, Ellis Horwood Limited, Chichester, England, 1984. (d) P. Gallezot, "Hydrogenation - Heterogeneous" in Encyclopedia of Catalysis, Volume 4, I. T. John Wiley & Sons, 2003. (e) J. G. de Vries, J. Cornelis Elsevier, “The Handbook of Homogeneous Hydrogenation” Wiley-VCH, Weinheim, 2007.
[3] (a) P. Magnus, M. J. Waring, D. A. Scott, Tetrahedron Lett. 41 (2000) 9731-9733. (b) V. Jurkauskas, J. P. Sadighi, S. L. Buchwald, Org. Lett. 5 (2003) 2417-2420. (c) B. H. Lipshutz, J. F. Servesko, T. B. Petersen, P. P. Papa, A. A. Lover, Org. Lett. 6 (2004) 1273-1275. (d) B. H. Lipshutz, J. M. Servesko, B. R. Taft, J. Am. Chem. Soc. 126 (2004) 8352-8353. (e) F. Alonso, I. Osante, M. Yus, Synlett, 18 (2006) 3017-3020. (f) N. J. A. Martin, B. List, J. Am. Chem. Soc. 128 (2006) 13368-13369. (g) Y. Kanazawa, H. Nishiyama, Synlett. 19 (2006) 3343-3345. (h) S. Chandrasekhar, G. Chandrashekar, M. S. Reddy, P. Srihari, Org. Bio. Chem. 4 (2006) 1650-1652. (i) B. A. Baker, A. V. Bokovi, B. H. Lipshutz, Org. Lett. 10 (2008) 289-292. (j) A. Pelss, E. T. T. Kumpulainen, A. R. M. Koskinen, J. Org. Chem. 74 (2009) 7598-7601. (k) Z. C. Duan, X. P. Hu, D. Y. Wang, S. B. Yu, Z. Zheng, Tetrahedron Lett. 50 (2009) 6720-6722.
[4] (a) L. Birkofer, E. Bierwirth, A. Ritter, Chem. Ber. 94 (1961) 821-824. (b) G. R. Pettit, R. L. Smith, A. K. Das Gupta, J. L. Occolowitz, Can. J. Chem. 45 (1966) 501-507. (c) L. H. Sommer, J. E. Lyons, J. Am. Chem. Soc. 89 (1967) 1521-1522. (d) L. H. Sommer, J. E. Lyons, J. Am. Chem. Soc. 91 (1969) 7061-7067. (e) J. D. Citron, J. E. Lyons, L. H. Sommer, J. Org. Chem. 34 (1969) 638-640. (f) A. Kunai, T. Sakurai, E. Toyoda, M. Ishikawa, Y. Yamamoto, Organometallics. 13 (1994) 3233-3236. (g) C. Ferreri, C. Costantino, R. Romeo, C. Chatgilialoglu, Tetrahedron Lett. 40 (1999) 1197-1200. (h) R. Boukherroub, C. Chatgilialoglu, G. Manuel, Organometallics. 15 (1996) 1508-1510. (i) C. Ferreri, C. Costantino, C. Chatgilialoglu, R. Boukherroub, G. Manuel, J. Organomet. Chem. 554 (1998)135-137.
[5] M. Mirza-Aghayan, R. Boukherroub, M. Bolourtchian, M. Hoseini, Tetrahedron Lett. 44 (2003) 4579-4580.
[6] M. Mirza-Aghayan, R. Boukherroub, M. Bolourtchian, K. Tabar-Hydar, M. Hoseini, J.Organomet. Chem. 678 (2003) 1-4.
[7] (a) M. Mirza-Aghayan, R. Boukherroub, M. Rahimifard, J. Organomet. Chem. 693 (2008) 3567-3570. (b) M. Mirza-Aghayan, R. Boukherroub, M. Rahimifard Tetrahedron Lett. 50 (2009) 5930-5932.
[8] P. V. Chouthaiwale, V. Rawat, G. Suryavanshi, A. Sudalai, Tetrahedron Lett. 53 (2012) 148-150.