European Journal of Chemistry 2018, 9(4), 317-321 | doi: https://doi.org/10.5155/eurjchem.9.4.317-321.1729 | Get rights and content

Issue cover




Crossmark

  Open Access OPEN ACCESS | Open Access PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

A mild and efficient method for the deprotection of trimethyl silyl alkynes using sodium ascorbate and copper sulphate


Ranjith Siddaraj (1) orcid , Raghu Ningegowda (2) orcid , Nanjunda Swamy Shivananju (3) orcid , Babu Shubha Priya (4,*) orcid

(1) Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570006, Karnataka, India
(2) Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570006, Karnataka, India
(3) Department of Biotechnology, Sri Jayachamarajendra College of Engineering, JSS Technical Institutions Campus, Mysore 570006, Karnataka, India
(4) Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570006, Karnataka, India
(*) Corresponding Author

Received: 03 May 2018 | Revised: 02 Jul 2018 | Accepted: 08 Jul 2018 | Published: 31 Dec 2018 | Issue Date: December 2018

Abstract


A competent and fast method for the deprotection of trimethyl silyl group was attained by using cheap, easily accessible, and nontoxic sodium ascorbate in combination with copper sulphate. The method labored was simple and effective for the cleavage of trimethyl silyl group from the protected trimethyl silyl alkynes to their corresponding alkyne derivatives. Wide functional group tolerance, shorter time period, simple procedure and high yields are the striking features of this protocol.


Announcements


Our editors have decided to support scientists to publish their manuscripts in European Journal of Chemistry without any financial constraints.

1- The article processing fee will not be charged from the articles containing the single-crystal structure characterization or a DFT study between September 15, 2023 and October 31, 2023 (Voucher code: FALL2023).

2. A 50% discount will be applied to the article processing fee for submissions made between September 15, 2023 and October 31, 2023 by authors who have at least one publication in the European Journal of Chemistry (Voucher code: AUTHOR-3-2023).

3. Young writers will not be charged for the article processing fee between September 15, 2023 and October 31, 2023 (Voucher code: YOUNG2023).

Editor-in-Chief
European Journal of Chemistry

Keywords


Deprotection; Ethanol-water; Copper sulphate; Protecting group; Sodium ascorbate; Trimethyl silyl alkyne

Full Text:

PDF
PDF    Open Access

DOI: 10.5155/eurjchem.9.4.317-321.1729

Links for Article


| | | | | | |

| | | | | | |

| | | |

Related Articles




Article Metrics

icon graph This Abstract was viewed 3807 times | icon graph PDF Article downloaded 985 times


Citations

/


[1]. Vijayakumar Uppar, Sandeep Chandrashekharappa, Mahendra K Mohan, Atiyaparveen I. Basarikattia, Beena B Rachotimath, Mallikarjun Chougala, Kiran K Mudnakudu-Nagaraju, Govindappa Bhanuprakash, Katharigatta N. Venugopala, Raghu Ningegowda, Basavaraj Padmashali
Synthesis and characterization of indolizine and 5,6-benzo-fused indolizine derivatives with their pharmacological applications
Chemical Data Collections  29, 100524, 2020
DOI: 10.1016/j.cdc.2020.100524
/

[2]. Werner Fudickar, Marcel Bauch, Heiko Ihmels, Torsten Linker
DNA‐Triggered Enhancement of Singlet Oxygen Production by Pyridinium Alkynylanthracenes
Chemistry – A European Journal  27(54), 13591, 2021
DOI: 10.1002/chem.202101918
/

References


[1]. Hajipur, A. R.; Mallapour, S. E.; Baltork, I. M. P. Indian J. Chem. 2002, 41, 1251-1256.

[2]. Wuts, P. G. M.; Greene, T. W., Protective Groups in Organic Synthesis, 4th edition, John Wiley & Sons, 2007.

[3]. Haiying J.; Guohua G. Arkivoc 2009, 12, 261-280.

[4]. Pierce, A. E., Silylation of Organic Compounds, Pierce Chemical Co., 1968.

[5]. Look, G. V.; Simchen, G.; Heberle, J., Silylating Agents, 2nd Edition, Fluka Chemicals, 1995.

[6]. Blau, K.; King, G. S., Handbook of derivatives for Chromatography, Heyden & Son Ltd., London, 1977.

[7]. Blau, K.; Halket, J., Handbook of derivatives for Chromatography, 2nd Edition, John Wiley & Son, 1993.

[8]. Knapp, D. R., Handbook of analytical derivatization reactions, John Wiley & Sons, 1979.

[9]. Colvin, E. W., Silicon in Organic Synthesis, Butterworth, 1981.

[10]. Greene, T. W., Protective Groups in Organic Synthesis, Wiley-Interscience, 1981.

[11]. Greene, T. W.; Wuts, P. G. M., Protective Groups in Organic Synthesis, 2nd Edition, Wiley-Interscience, 1991.

[12]. Cooper, B. E. Chem. Ind. 1978, 20, 794-797.

[13]. Brownbridge, P. Synthesis 1983, 2, 85-104.
https://doi.org/10.1055/s-1983-30234

[14]. Lalonde, M.; Chan, T. H. Synthesis 1985, 9, 814-845.

[15]. Olsson, L. I. Acta Pharm. Suec. 1986, 23, 370-385.

[16]. Kuwajima, I.; Nakamura, E. Acc. Chem. Res. 1985, 18, 181-187.
https://doi.org/10.1021/ar00114a004

[17]. Lukevics, E. Russ. Chem. Rev. 1974, 43, 140-154.
https://doi.org/10.1070/RC1974v043n02ABEH001796

[18]. Shirai, N.; Moriya, K.; Kawazoe, Y. Tetrahedron 1986, 42, 2211-2214.
https://doi.org/10.1016/S0040-4020(01)90600-3

[19]. Kawazoe, Y.; Nomura, M.; Kondo, Y.; Kohda, K. Tetrahedron Lett. 1987, 28, 4307-4310.
https://doi.org/10.1016/S0040-4039(00)96492-X

[20]. Voaden, D. J.; Waters, R. M. Org. Prep. Proced. Int. 1976, 8, 227-230.
https://doi.org/10.1080/00304947609355630

[21]. Kierzek, R. Nucleosides Nucleotides 1985, 4, 641-649.
https://doi.org/10.1080/07328318508081896

[22]. Jung, M. E. J. Org. Chem 1976, 41, 1479-1480.
https://doi.org/10.1021/jo00870a047

[23]. Jung, M. E.; Speltz, L. M. J. Am. Chem. Soc. 1976, 98, 7882-7884.
https://doi.org/10.1021/ja00440a102

[24]. Pinnick, H. W.; Laujis, N. H. J. Org. Chem. 1978, 43, 371-372.
https://doi.org/10.1021/jo00396a054

[25]. Hergott, H. H.; Simchen, G. Liebigs Ann. Chem. 1980, 11, 1718-1721.
https://doi.org/10.1002/jlac.198019801110

[26]. Cooper, B. E.; Westall, S. J. Organomet. Chem. 1976, 118, 135-138.
https://doi.org/10.1016/S0022-328X(00)92148-X

[27]. Kita, Y.; Haruta, J.; Segawa, J.; Tamura, Y. Tetrahedron Lett. 1979, 20, 4311-4314.
https://doi.org/10.1016/S0040-4039(01)86575-8

[28]. Murata, S.; Noyori, R. Tetrahedron Lett. 1980, 21, 767-768.
https://doi.org/10.1016/S0040-4039(00)71468-7

[29]. Piekos, P. J. Chromatogr. 1976, 116, 315-320.
https://doi.org/10.1016/S0021-9673(00)89902-1

[30]. Aizpurua, J. M.; Palomo, C. Synthesis 1982, 8, 684-687.
https://doi.org/10.1055/s-1982-29903

[31]. Tanabe, Y.; Murakami, M.; Kitaichi, K.; Yoshida, Y. Tetrahedron Lett. 1994, 35, 8409-8412.
https://doi.org/10.1016/S0040-4039(00)74419-4

[32]. Orsini, A.; Viterisi, A.; Bodlenner, A.; Weibel, J. M.; Pale, P. Tetrahedron Lett. 2005, 46, 2259-2262.
https://doi.org/10.1016/j.tetlet.2005.02.017

[33]. Ishita, H.; Raja, M.; Kalyan, S.; Amit, B. Tetrahedron Lett. 2015, 56, 4275-4279.
https://doi.org/10.1016/j.tetlet.2015.04.104

[34]. Shultz, D. A.; Gwaleney, K. P. J. Org. Chem. 1998, 63, 4034-4038.
https://doi.org/10.1021/jo980098o

[35]. Yeom, C. E.; Kim, M. J.; Choi, W.; Kim, B. M. Synlett. 2008, 4, 565-568.

[36]. Aucagne, V.; Leigh, D. A. Org. Lett. 2006, 8, 4505-4507.
https://doi.org/10.1021/ol061657d

[37]. Slutsky, M. M.; Phillip, J. S.; Tew, G. N. New J. Chem. 2008, 32, 670-675.
https://doi.org/10.1039/b707618e

[38]. Fletcher, J. T.; Walz, S. E.; Keeney, M. E. Tetrahedron Lett. 2008, 49, 7030-7032.
https://doi.org/10.1016/j.tetlet.2008.09.136


How to cite


Siddaraj, R.; Ningegowda, R.; Shivananju, N.; Priya, B. Eur. J. Chem. 2018, 9(4), 317-321. doi:10.5155/eurjchem.9.4.317-321.1729
Siddaraj, R.; Ningegowda, R.; Shivananju, N.; Priya, B. A mild and efficient method for the deprotection of trimethyl silyl alkynes using sodium ascorbate and copper sulphate. Eur. J. Chem. 2018, 9(4), 317-321. doi:10.5155/eurjchem.9.4.317-321.1729
Siddaraj, R., Ningegowda, R., Shivananju, N., & Priya, B. (2018). A mild and efficient method for the deprotection of trimethyl silyl alkynes using sodium ascorbate and copper sulphate. European Journal of Chemistry, 9(4), 317-321. doi:10.5155/eurjchem.9.4.317-321.1729
Siddaraj, Ranjith, Raghu Ningegowda, Nanjunda Swamy Shivananju, & Babu Shubha Priya. "A mild and efficient method for the deprotection of trimethyl silyl alkynes using sodium ascorbate and copper sulphate." European Journal of Chemistry [Online], 9.4 (2018): 317-321. Web. 23 Sep. 2023
Siddaraj, Ranjith, Ningegowda, Raghu, Shivananju, Nanjunda, AND Priya, Babu. "A mild and efficient method for the deprotection of trimethyl silyl alkynes using sodium ascorbate and copper sulphate" European Journal of Chemistry [Online], Volume 9 Number 4 (31 December 2018)

The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item



DOI Link: https://doi.org/10.5155/eurjchem.9.4.317-321.1729


CrossRef | Scilit | GrowKudos | Researchgate | Publons | ScienceGate | Scite | Lens | OUCI

WorldCat Paperbuzz | LibKey Citeas | Dimensions | Semanticscholar | Plumx | Kopernio | Zotero | Mendeley

ZoteroSave to Zotero MendeleySave to Mendeley



European Journal of Chemistry 2018, 9(4), 317-321 | doi: https://doi.org/10.5155/eurjchem.9.4.317-321.1729 | Get rights and content

Refbacks

  • There are currently no refbacks.


Bookmark and Share


Copyright (c) 2018 Authors

Creative Commons License
This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at http://www.eurjchem.com/index.php/eurjchem/pages/view/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (http://www.eurjchem.com/index.php/eurjchem/pages/view/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).


© Copyright 2010 - 2023 • Atlanta Publishing House LLC • All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2010-2023 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.