Studies on the Deprotection of Triisopropylsilylarylacetylene Derivatives

Authors

  • Ismael Valois Escamilla Universidad Autónoma del Estado de Hidalgo
  • Luis Felipe Rangel Ramos Universidad Autónoma del Estado de Hidalgo
  • Javier Sánchez Escalera Universidad Autónoma del Estado de Hidalgo
  • Alejandro Álvarez Hernández Universidad Autónoma del Estado de Hidalgo

DOI:

https://doi.org/10.29356/jmcs.v55i3.810

Keywords:

Desylylation, silver fluoride, alkyne protecting group, TIPS-acetylene.

Abstract

Several conditions to deprotect triisopropylsilylarylacetylenes were examined. The triisopropylsilyl protecting group was efficiently removed under mild conditions with 1.5 equiv. of AgF in methanol, a protocol recently reported by Kim. A mixture of AgNO3/KF gave lower yields. Other conditions using combinations of a transition metal, Cu(I), Co(II), Hg(II), and KF failed to react or produced decomposition. The AgF deprotection of TIPS-acetylenes allowed preparation of aryl and heteroaryl terminal alkynes.

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Author Biographies

Ismael Valois Escamilla, Universidad Autónoma del Estado de Hidalgo

Centro de Investigaciones Químicas

Luis Felipe Rangel Ramos, Universidad Autónoma del Estado de Hidalgo

Centro de Investigaciones Químicas

Javier Sánchez Escalera, Universidad Autónoma del Estado de Hidalgo

Centro de Investigaciones Químicas

Alejandro Álvarez Hernández, Universidad Autónoma del Estado de Hidalgo

Centro de Investigaciones Químicas

References

Kru?ger, K.; Tillack, A.; Beller, M. Adv. Synth. Catal. 2008, 350, 2153-2167.

Bunz, U. H. F., Chem. Rev. 2000, 100, 1605-1644.

Wegner, G.; Mu?llen, K., Electronic Materials: The Oligomer Approach. Wiley-VCH, Ed. Weinheim, 1998.

Chinchilla, R.; Nájera, C. Chem. Rev. 2007, 107, 874-922.

Heravi, M. M.; Sadjadi, S. Tetrahedron 2009, 65, 7761-7775.

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

Sonogashira, K. J. Organomet. Chem. 2002, 653, 46-49.

Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467-4470.

Doucet, H.; Hierso, J. C. Angew. Chem. Int. Ed. 2007, 46, 834-871.

Tykwinski, R. R. Angew. Chem. Int. Ed. 2003, 42, 1566-1568.

Jin, M. J.; Lee, D. H. Angew. Chem. Int. Ed. 2010, 49, 1119-1122.

Lipshutz, B. H.; Chung, D. W.; Rich, B. Org. Lett. 2008, 10, 3793-3796.

Trost, B. M. Angew. Chem. Int. Ed. 1995, 34, 259-281.

Trost, B. M. Acc. Chem. Res. 2002, 35, 695-705.

Kim, S.; Kim, S.; Lee, T.; Ko, H.; Kim, D. Org. Lett. 2004, 6, 3601-3604.

Kim, S.; Lee, Y. M.; Kang, H. R.; Cho, J.; Lee, T.; Kim, D. Org.Lett. 2007, 9, 2127-2130.

Marino, J. P.; Nguyen, H. N. J. Org. Chem. 2002, 67, 6841-6844.

Heuft, M. A.; Collins, S. K.; Yap, G. P. A.; Fallis, A. G. Org. Lett.2001, 3, 2883-2886.

Csékei, M.; Novák, Z.; Kotschy, A. Tetrahedron 2008, 64, 975-982.

Melissaris, A. P.; Litt, M. H. J. Org. Chem. 1994, 59, 5818-5821.

Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, Third Edition. John Wiley & Sons Inc, New York, 1999.

Wang, C.; Batsanov, A. S.; Bryce, M. R. J. Org. Chem. 2006, 71, 108-116.

Kim, S.; Kim, B.; In, J. Synthesis 2009, 1963-1968.

Moon, J.; Jeong, M.; Nam, H.; Ju, J.; Moon, J. H.; Jung, H. M.; Lee, S. Org. Lett. 2008, 10, 945-948.

Takahashi, S.; Kuroyama, Y.; Sonogashira, K.; Hagihara, N., Synthesis 1980, 627-630.

Richardson, C.; Reed, C. A. J. Org. Chem. 2007, 72, 4750-4755.

Ziessel, R.; Suffert, J.; Youinou, M. T. J. Org. Chem. 1996, 61, 6535-6546.

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Published

2019-03-25

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Regular Articles