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Synlett 2010(12): 1870-1872
DOI: 10.1055/s-0030-1258122
DOI: 10.1055/s-0030-1258122
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New YorkHighly Selective Semihydrogenation of Phenylalkynes to (Z)-Styrenes Using Hantzsch Ester 1,4-Dihydropyridine Catalyzed by Pd/C
Further Information
Received
1 March 2010
Publication Date:
30 June 2010 (online)
Publication History
Publication Date:
30 June 2010 (online)

Abstract
Various alkynes have been selectively reduced to the corresponding Z-alkenes catalyzed by Pd/C using Hantzsch ester 1,4-dihydropyridine as the hydrogen source.
Key words
alkynes - alkenes - palladium - reduction - regioselectivity
- Supporting Information for this article is available online:
- Supporting Information
- 1a
Rylander PN. Catalytic Hydrogenation in Organic Syntheses Academic Press; New York: 1979. - 1b
Siegel S. In Comprehensive Organic Synthesis Vol. 8:Trost BM.Fleming I. Pergamon Press; Oxford: 1991. Chap. 3.1. - 1c
Takaya H.Noyori R. In Comprehensive Organic Synthesis Vol. 8:Trost BM.Fleming I. Pergamon Press; Oxford: 1991. Chap. 3.2. - 1d
Nishimura S. In Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis Wiley-Interscience; New York: 2001. - 1e
Molnár .Sárkány A.Varga M. J. Mol. Catal. A: Chem. 2001, 173: 185 - 1f
Kluwer AM.Elsevier CJ. In The Handbook of Homogeneous Hydrogenation Vol. 1:Vries JG.Elsevier CJ. Wiley-VCH; Weinheim: 2007. p.375-411 - 2a
Lindlar H. Helv. Chim. Acta 1952, 35: 446 - 2b
Lindlar H.Dubuis R. Org. Synth., Coll. Vol. V 1973, 880 - 2c
Choudary BM.Sharma GVM.Bharathi P. Angew. Chem., Int. Ed. Engl. 1989, 28: 465 - 2d
Schmid G.Harns M.Malm JO.Bovin JO.Ruitenbeck JV.Zandbergen HW.Fu WT. J. Am. Chem. Soc. 1993, 115: 2046 - 2e
Yu J.Spencer JB. Chem. Commun. 1998, 1103 - 2f
Campos KR.Cai D.Journet M.Kowal JJ.Larsen RD.Reider PJ. J. Org. Chem. 2001, 66: 3634 - 2g
van Laren MW.Duin MA.Klerk C.Naglia M.Rogolino D.Pelagatti P.Bacchi A.Pelizzi C.Elsevier CJ. Organometallics 2002, 21: 1546 - 2h
Bronstein LM.Chernyshov DM.Karlinsey R.Zwanziger JW.Matveeva VG.Sulman EM.Demidenko GN.Hentze H.-P.Antonietti M. Chem. Mater. 2003, 15: 2623 - 2i
Sprengers JW.Wassenaar J.Clement ND.Cavell KJ.Elsevier CJ. Angew. Chem. Int. Ed. 2005, 44: 2026 - 2j
Kluwer AM.Koblenz TS.Jonischkeit T.Woelk K.Elsevier CJ. J. Am. Chem. Soc. 2005, 127: 15470 - 2k
Nishio R.Sugiura M.Kobayash S. Org. Biomol. Chem. 2006, 4: 992 - 2l
Hauwert P.Maestri G.Sprengers JW.Catellani M.Elsevier CJ. Angew. Chem. 2008, 120: 3267 - 2m
Sajiki H.Mori S.Ohkubo T.Ikawa T.Kume A.Maegawa T.Monguchi Y. Chem. Eur. J. 2008, 14: 5109 - 2n
Hori J.Murata K.Sugai T.Shinohara H.Noyori R.Arai N.Kurono N.Ohkuma T. Adv. Synth. Catal. 2009, 351: 3143 - 3a
Brown CA.Ahuja VK. Chem. Commun. 1973, 553 - 3b
Brown CA.Ahuja VK. J. Org. Chem. 1973, 38: 2226 - 3c
Savoia D.Tagliavini E.Trombini C.Umani-Ronchi A. J. Org. Chem. 1981, 46: 5340 - 3d
Choi J.Yoon NM. Tetrahedron Lett. 1996, 37: 1057 - 3e
Alonso F.Osante I.Yus M. Adv. Synth. Catal. 2006, 348: 305 - 4a
Albers MO.Singleton E.Viney MM. J. Mol. Catal. 1985, 30: 213 - 4b
Suares T.Fontal B. J. Mol. Catal. 1988, 45: 335 - 4c
Bianchini C.Bohanna C.Esteruelas MA.Frediani P.Meli A.Oro LA.Peruzzini M. Organometallics 1992, 11: 3837 - 4d
Trost BM.Ball ZT.Jöge T. J. Am. Chem. Soc. 2002, 124: 7922 - 5a
Schrock RR.Osborn JA. J. Am. Chem. Soc. 1976, 98: 2143 - 5b
Sodeoka M.Shibasaki M. J. Org. Chem. 1985, 50: 1147 - 6
Segura Y.López N.Pérez-Ramírez J. J. Catal. 2007, 247: 383 - 7a
van Laren MW.Elsevier CJ. Angew. Chem. Int. Ed. 1999, 38: 3715 - For selected examples, see:
- 8a
Zhu X.-Q.Wang H.-Y.Wang J.-S.Liu Y.-C. J. Org. Chem. 2000, 66: 344 - 8b
Ouellet SG.Tuttle JB.MacMillan DWC. J. Am. Chem. Soc. 2004, 127: 32 - 8c
Yang JW.Fonseca M TH.List B. Angew. Chem. Int. Ed. 2004, 43: 6660 - 8d
Hoffmann S.Seayad AM.List B. Angew. Chem. Int. Ed. 2005, 44: 7424 - 8e
Rueping M.Sugiono E.Azap C.Theissmann T.Bolte M. Org. Lett. 2005, 7: 3781 - 8f
Storer RI.Carrera DE.Ni Y.MacMillan DWC. J. Am. Chem. Soc. 2005, 128: 84 - 8g
Hoffmann S.Nicoletti M.List B. J. Am. Chem. Soc. 2006, 128: 13074 - 8h
Martin NJA.List B. J. Am. Chem. Soc. 2006, 128: 13368 - 8i
Mayer S.List B. Angew. Chem. Int. Ed. 2006, 45: 4193 - 8j
Menche D.Hassfeld J.Li J.Menche G.Ritter A.Rudolph S. Org. Lett. 2006, 8: 741 - 8k
Tuttle JB.Ouellet SG.MacMillan DWC. J. Am. Chem. Soc. 2006, 128: 12662 - 8l
Yang JW.List B. Org. Lett. 2006, 8: 5653 - 8m
Barbe G.Charette AB. J. Am. Chem. Soc. 2007, 130: 18 - 8n
Li G.Liang Y.Antilla JC. J. Am. Chem. Soc. 2007, 129: 5830 - 8o
Martin NJA.Ozores L.List B. J. Am. Chem. Soc. 2007, 129: 8976 - 8p
Kang Q.Zhao Z.-A.You S.-L. Org. Lett. 2008, 10: 2031 - 8q
Liu Z.Han B.Liu Q.Zhang W.Yang L.Liu Z.-L.Yu W. Synlett 2005, 1579 - 8r
Liu Z.Liu Q.Zhang W.Mu R.Yang L.Liu Z.-L.Yu W. Synthesis 2006, 771 - 8s
Shen XX.Liu Q.Xing R.-G.Zhou B. Catal Lett. 2008, 126: 361 - 8t
Liu Q.Li J.Shen XX.Xing RG.Yang J.Liu Z.Zhou B. Tetrahedron Lett. 2009, 50: 1026 - 8u
Meng Q.Liu Q.Li J.Xing RG.Shen XX.Zhou B. Synlett 2009, 3283 - 9
Zhang D.Wu L.-Z.Zhou L.Han X.Yang Q.-Z.Zhang L.-P.Tung C.-H. J. Am. Chem. Soc. 2004, 126: 3440 - 11
Schwarz DE.Cameron TM.Hay PJ.Scott BL.Tumas W.Thorn DL. Chem. Commun. 2005, 5919
References and Notes
For details see the Supporting Information.