Download PDF
Banert, K. et al.: 2014 Science of Synthesis, 2014/3: Knowledge Updates 2014/3 DOI: 10.1055/sos-SD-124-00151
Knowledge Updates 2014/3

24.3.12 Bis(heteroatom-functionalized) Acetylenes (Update 2014)

More Information

Book

Editors: Banert, K.; Brøndsted Nielsen, M.; Drabowicz, J.; Joule, J. A.; Schaumann, E.; Weinreb, S. M.

Authors: Aitken, R. A.; Ameduri, B.; Braverman, S.; Brøndsted Nielsen, M.; Cherkinsky, M.; Heydt, H.; Meehan, A.; Petersen, A. U.; Polo, A.; Real, J.; Stanforth, S. P.; Udmark, J.

Title: Knowledge Updates 2014/3

Print ISBN: 9783131762818; Online ISBN: 9783131975119; Book DOI: 10.1055/b-003-125830

1st edition © 2014 Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

Science of Synthesis Knowledge Updates



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Carreira, E. M.; Decicco, C. P.; Fürstner, A.; Molander, G. A.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.

Type: Multivolume Edition

Also available at
 


Abstract

This chapter provides an update to the earlier Science of Synthesis contribution (Section 24.3) describing methods for the synthesis of bis(heteroatom-functionalized) acetylenes. Selected applications are also included. It focuses on the literature published since the original report in 2006 up until the end of 2013.

Key words

alkynes - alkynes - cross-coupling reactions - dehydrohalogenation - halogenation - nucleophilic substitution
 
  • 3 Salzer A, Severins C. WO 2 008 055 963, 2008
  • 9 Wuts PGM, Greene TW. Greene’s Protective Groups in Organic Synthesis. 4th ed., Wiley; Hoboken, NJ 2007: 927-933
    Search in Google Scholar
  • 11 Kawai H, Utamura T, Motoi E, Takahashi T, Sugino H, Tamura M, Ohkita M, Fujiwara K, Saito T, Tsuji T, Suzuki T. Chem.–Eur. J. 2013; 19: 4513
    Search in Google Scholar
  • 16 Klinger C, Vostrowsky O, Hirsch A. Eur. J. Org. Chem. 2006; 1508
  • 17 Cataldo F, Ursini O, Angelini G, Tommasini M, Casari C. J. Macromol. Sci., Part A: Pure Appl. Chem. 2010; 47: 739
    Search in Google Scholar
  • 18 Cataldo F, Ravagnan L, Cinquanta E, Castelli IE, Manini N, Onida G, Milani P. J. Phys. Chem. B 2010; 114: 14 834
    Search in Google Scholar
  • 31 Zhang X, Zhang Y, Huang J, Hsung RP, Kurtz KCM, Oppenheimer J, Petersen ME, Sagamanova IK, Shen L, Tracey MR. J. Org. Chem. 2006; 71: 4170
    Search in Google Scholar
  • 36 Poulsen TB, Bernardi L, Alemán J, Overgaard J, Jørgensen KA. J. Am. Chem. Soc. 2007; 129: 441
    Search in Google Scholar
  • 40 Märkl G, Zollitsch T, Kreitmeier P, Prinzhorn M, Reithinger S, Eibler E. Chem.–Eur. J. 2000; 6: 3806
    Search in Google Scholar
  • 41 Padovan P, Tartaggia S, Lorenzon S, Rosso E, Zonta C, De Lucchi O, Fabris F. Tetrahedron Lett. 2009; 50: 1973
    Search in Google Scholar
  • 42 Saunders BC, Simpson P. J. Chem. Soc. 1963; 3351
  • 45 Hoshi M, Kawamura N, Shirakawa K. Synthesis 2006; 1961
  • 46 Hoshi M, Iizawa T, Okimoto M, Shirakawa K. Synthesis 2008; 3591
  • 48 Gulia N, Osowska K, Pigulski B, Lis T, Galewski Z, Szafert S. Eur. J. Org. Chem. 2012; 4819
  • 51 Amemiya R, Suwa K, Toriyama J, Nishimura Y, Yamaguchi M. J. Am. Chem. Soc. 2005; 127: 8252
    Search in Google Scholar
  • 55 Khramchikhin VA, Yacobson GV, Dogadina AV, Khramchikhin AV, Ionin BI. Russ. J. Gen. Chem. (Engl. Transl.) 2010; 80: 364
    Search in Google Scholar
  • 56 Khramchikhin VA, Didkovskii NG, Khramchikhin AV, Dogadina AV, Ionin BI. Russ. J. Gen. Chem. (Engl. Transl.) 2011; 81: 1635
    Search in Google Scholar
  • 57 Khramchikhin VA, Dogadina AV, Khramchikhin AV, Ionin BI. Russ. J. Gen. Chem. (Engl. Transl.) 2012; 82: 776
    Search in Google Scholar
  • 58 Petryanina AI, Didkovskii NG, Dogadina AV, Ionin BI. Russ. J. Gen. Chem. (Engl. Transl.) 2006; 76: 1516
    Search in Google Scholar
  • 59 Erkhitueva EB, Dogadina AV, Khramchikhin AV, Ionin BI. Russ. J. Org. Chem. (Engl. Transl.) 2013; 49: 580
    Search in Google Scholar
  • 61 Erkhitueva EB, Dogadina AV, Khramchikhin AV, Ionin BI. Russ. J. Gen. Chem. (Engl. Transl.) 2011; 81: 2377
    Search in Google Scholar
  • 62 Erkhitueva EB, Egorov DM, Dogadina AV, Khramchikhin AV, Ionin BI. Russ. J. Gen. Chem. (Engl. Transl.) 2012; 82: 2011
    Search in Google Scholar
  • 64 Moreno-Clavijo E, Moreno-Vargas AJ, Carmona AT, Robina I. Org. Biomol. Chem. 2013; 11: 7016
    Search in Google Scholar
  • 65 Moreno-Clavijo E, Moreno-Vargas AJ, Kieffer R, Sigstam T, Carmona AT, Robina I. Org. Lett. 2011; 13: 6244
    Search in Google Scholar
  • 69 Allen A, Villeneuve K, Cockburn N, Fatila E, Riddell N, Tam W. Eur. J. Org. Chem. 2008; 4178
  • 71 Seidel WW, Meel MJ, Schaffrath M, Pape T. Eur. J. Org. Chem. 2007; 3526
  • 78 Gleiter R, Schulte JH, Werz DB. Eur. J. Org. Chem. 2004; 4077
  • 79 Melzig L, Stemper J, Knochel P. Synthesis 2010; 2085
  • 81 Pellizzaro L, Cabianca E, Tatibouët A, Padovan P, Fabris F, Rollin P, De Lucchi O. Tetrahedron Lett. 2007; 48: 3699
    Search in Google Scholar
  • 84 D’yachkova SG, Nikitina EA, Gusarova NK, Al’pert ML, Trofimov BA. Russ. Chem. Bull. 2001; 50: 751
    Search in Google Scholar
  • 85 D’yachkova SG, Nikitina EA, Gusarova NK, Albanov AI, Trofimov BA. Russ. J. Gen. Chem. (Engl. Transl.) 2003; 73: 782
    Search in Google Scholar
  • 87 Banert K, Hagedorn M, Wutke J, Ecorchard P, Schaarschmidt D, Lang H. Chem. Commun. (Cambridge) 2010; 46: 4058
    Search in Google Scholar
  • 88 Voronkov MG, Lebedeva IP, Rakhlin VI, D’yachkova SG. ARKIVOC 2005; vii, 56
  • 93 Rodríguez D, Martínez-Esperón MF, Castedo L, Saá C. Synlett 2007; 1963
  • 95 Svintsitskaya NI, Aleksandrova AV, Dogadina AV, Ionin BI. Russ. J. Gen. Chem. (Engl. Transl.) 2008; 78: 157
    Search in Google Scholar
  • 96 Svintsitskaya NI, Aimakov OA, Dogadina AV, Ionin BI. Russ. J. Gen. Chem. (Engl. Transl.) 2009; 79: 1461
    Search in Google Scholar
  • 100 van Assema SGA, Kraikivskii PB, Zelinskii SN, Saraev VV, de Jong GB, de Kanter FJJ, Schakel M, Slootweg JC, Lammertsma K. J. Organomet. Chem. 2007; 692: 2314
    Search in Google Scholar
  • 103 Banert K, Köhler F, Melzer A, Scharf I, Rheinwald G, Rüffer T, Lang H, Herges R, Heß K, Ghavtadze N, Würthwein E.-U. Chem.–Eur. J. 2011; 17: 10 071
    Search in Google Scholar
  • 104 Banert K, Köhler F, Melzer A, Scharf I, Rheinwald G, Rüffer T, Lang H. Synthesis 2011; 1561
  • 105 Persich P, Llaveria J, Lhermet R, de Haro T, Stade R, Kondoh A, Fürstner A. Chem.–Eur. J. 2013; 19: 13 047
    Search in Google Scholar
  • 106 Nagaki A, Matsuo C, Kim S, Saito K, Miyazaki A, Yoshida J.-i. Angew. Chem. Int. Ed. 2012; 51: 3245
    Search in Google Scholar
  • 107 Panarina AE, Aleksandrova AV, Dogadina AV, Ionin BI. Russ. J. Gen. Chem. (Engl. Transl.) 2005; 75: 3
    Search in Google Scholar
  • 108 Aleksandrova AV, Dogadina AV, Ionin BI. Russ. J. Gen. Chem. (Engl. Transl.) 2005; 75: 1664
    Search in Google Scholar
  • 109 Panarina AE, Aleksandrova AV, Dogadina AV, Ionin BI. Russ. J. Gen. Chem. (Engl. Transl.) 2004; 74: 1459
    Search in Google Scholar
  • 110 Svintsitskaya NI, Aleksandrova AV, Dogadina AV, Ionin BI. Russ. J. Gen. Chem. (Engl. Transl.) 2007; 77: 963
    Search in Google Scholar
  • 111 Svintsitskaya NI, Dogadina AV, Ionin BI. Russ. J. Gen. Chem. (Engl. Transl.) 2008; 78: 2031
    Search in Google Scholar
  • 112 Shekhadeh A, Didkovskii NG, Dogadina AV, Ionin BI. Russ. J. Gen. Chem. (Engl. Transl.) 2005; 75: 9
    Search in Google Scholar
  • 113 Didkovskii NG, Petryanina AI, Dogadina AV, Ionin BI. Russ. J. Gen. Chem. (Engl. Transl.) 2006; 76: 1512
    Search in Google Scholar
  • 114 Duda B, Tverdomed SN, Ionin BI, Röschenthaler G.-V. Eur. J. Org. Chem. 2012; 3684
  • 118 Tverdomed SN, Röschenthaler G.-V, Kalinovich N, Lork E, Dogadina AV, Ionin BI. Tetrahedron 2008; 64: 5306
    Search in Google Scholar
  • 119 Artyushin OI, Matveeva EV, Bushmarinov IS, Odinets IL. ARKIVOC 2012; iv, 252