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Aitken, R. A. et al.: 2016 Science of Synthesis, 2015/2: Knowledge Updates 2015/2 DOI: 10.1055/sos-SD-124-00244
Knowledge Updates 2015/2

24.4.2.3 1-(Organooxy)alk-1-ynes and 1-(Heterooxy)alk-1-ynes (Update 2015)

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Book

Editors: Aitken, R. A.; Brønsted Nielsen, M.; Drabowicz, J.; Li, J. J.; Plietker, B.; Wirth, T.

Authors: Banert, K.; Brønsted Nielsen, M.; Cacciarini, M.; Elliott, M.; Grün, A.; Hagen, T.; Helgren, T.; Hennecke, U.; Iskra, J.; Kang, F.-A.; Keglevich, G.; Larsen, M. H.; Li, H.; Mazet, C.; Murphree, S.S.; Nomoto, A.; Ogawa, A.; Reißig, H.-U.; Saleh, B. A.; Singh, F. V. ; Tomé, A. C.; Wirth, T.; Yang, S.-M.; Zimmer, R.

Title: Knowledge Updates 2015/2

Print ISBN: 9783131984616; Online ISBN: 9783131975812; Book DOI: 10.1055/b-003-125870

1st Edition © 2016 Georg Thieme Verlag KG
Georg Thieme Verlag, 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.; Koch, G.; Molander, G.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.

Type: Multivolume Edition

Also available at
 

Abstract

This manuscript is an update to the earlier Science of Synthesis contribution (Section 24.4.2) describing methods for the synthesis of 1-(organooxy)alk-1-ynes and 1-(heterooxy)alk-1-ynes. The original contribution describes the synthesis of six subgroups: alk-1-ynyl N,N-dialkylcarbamates, carboxylates, ethers, sulfonates, and dialkyl phosphonates as well as 1-siloxyalk-1-ynes. However, during the period covered in this update (2005–2014), new contributions have only been made in the field of alk-1-ynyl ethers and 1-siloxyalk-1-ynes. These methodologies, primarily methods centering on elimination reactions, are covered in this chapter, along with a short description of the applications of these two types of compound.

Key words

alkynyl ethers - siloxyalkynes - elimination - Meyer–Schuster rearrangement - metal catalysis
 
  • 1 Tran V., Minehan T. G. Org. Lett. 2011; 13: 6588
  • 2 Hashmi A. S. K., Rudolph M., Bats J. W., Frey W., Rominger F., Oeser T. Chem.–Eur. J. 2008; 14: 6672
  • 3 Hashmi A. S. K., Rudolph M., Huck J., Frey W., Bats J. W., Hamzić M. Angew. Chem. Int. Ed. 2009; 48: 5848
  • 4 Komine Y., Tanaka K. Org. Lett. 2010; 12: 1312
  • 5 Graf K., Rühl C. L., Rudolph M., Rominger F., Hashmi A. S. K. Angew. Chem. Int. Ed. 2013; 52: 12 727
  • 6 Engel D. A., Dudley G. B. Org. Lett. 2006; 8: 4027
  • 7 Lopez S. S., Engel D. A., Dudley G. B. Synlett 2007; 949
  • 8 Engel D. A., Lopez S. S., Dudley G. B. Tetrahedron 2008; 64: 6988
  • 9 Puri S., Thirupathi N., Reddy M. S. Org. Lett. 2014; 16: 5246
  • 10 Egi M., Ota Y., Nishimura Y., Shimizu K., Azechi K., Akai S. Org. Lett. 2013; 15: 4150
  • 11 Verrier C., Carret S., Poisson J.-F. Monatsh. Chem. 2013; 144: 455
  • 12 Verrier C., Carret S., Poisson J.-F. Org. Biomol. Chem. 2014; 12: 1875
  • 13 Tohyama S., Choshi T., Azuma S., Fujioka H., Hibino S. Heterocycles 2009; 79: 955
  • 14 Muthusamy S., Babu S. A., Gunanathan C. Tetrahedron Lett. 2002; 43: 3133
  • 15 Sosa J. R., Tudjarian A. A., Minehan T. G. Org. Lett. 2008; 10: 5091
  • 16 Gray V. J., Cuthbertson J., Wilden J. D. J. Org. Chem. 2014; 79: 5869
  • 17 Marzo L., Parra A., Frías M., Alemán J., García Ruano J. L. Eur. J. Org. Chem. 2013; 4405
  • 18 Jouvin K., Bayle A., Legrand F., Evano G. Org. Lett. 2012; 14: 1652
  • 19 Jouvin K., Coste A., Bayle A., Legrand F., Karthikeyan G., Tadiparthi K., Evano G. Organometallics. 2012; 31: 7933
  • 20 Julia M., Saint-Jalmes V. P., Verpeaux J.-N. Synlett 1993; 233
  • 21 Sweis R. F., Schramm M. P., Kozmin S. A. J. Am. Chem. Soc. 2004; 126: 7442
  • 22 Shubinets V., Schramm M. P., Kozmin S. A. Org. Synth. 2010; 87: 253
  • 23 Türkmen Y. E., Montavon T. J., Kozmin S. A., Rawal V. H. J. Am. Chem. Soc. 2012; 134: 9062
  • 24 Montavon T. J., Türkmen Y. E., Shamsi N. A., Miller C., Sumaria C. S., Rawal V. H., Kozmin S. A. Angew. Chem. Int. Ed. 2013; 52: 13 576
  • 25 Zhao W., Wang Z., Sun J. Angew. Chem. Int. Ed. 2012; 51: 6209
  • 26 Zhang L., Kozmin S. A. J. Am. Chem. Soc. 2004; 126: 10 204
  • 27 Zhang L., Kozmin S. A. J. Am. Chem. Soc. 2004; 126: 11 806
  • 28 Zhang L., Sun J., Kozmin S. A. Tetrahedron 2006; 62: 11 371
  • 29 Sun J., Conley M. P., Zhang L., Kozmin S. A. J. Am. Chem. Soc. 2006; 128: 9705
  • 30 Austin W. F., Zhang Y., Danheiser R. L. Org. Lett. 2005; 7: 3905
  • 31 Austin W. F., Zhang Y., Danheiser R. L. Tetrahedron 2008; 64: 915
  • 32 Sun J., Kozmin S. A. Angew. Chem. Int. Ed. 2006; 45: 4991
  • 33 Sun J., Keller V. A., Meyer S. T., Kozmin S. A. Adv. Synth. Catal. 2010; 352: 839
  • 34 Montavon T. J., Li J., Cabrera-Pardo J. R., Mrksich M., Kozmin S. A. Nat. Chem. 2012; 4: 45
  • 35 Meyer K. H., Schuster K. Ber. Dtsch. Chem. Ges. B 1922; 55: 819