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Synthesis 2019; 51(22): 4153-4164
DOI: 10.1055/s-0039-1690184
paper
© Georg Thieme Verlag Stuttgart · New York

2-(3-Cyanopropyldimethylsilyl)ethyl as a Polar Sulfur Protecting Group

Linda M. Bannwart
a   Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056 Basel, Switzerland   Email: marcel.mayor@unibas.ch
,
Pascal S. Rieder
a   Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056 Basel, Switzerland   Email: marcel.mayor@unibas.ch
,
Marcel Mayor∗
a   Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056 Basel, Switzerland   Email: marcel.mayor@unibas.ch
b   Institute for Nanotechnology (INT), Karlsruhe Institute of Technology (KIT), P.O. Box 3640, 76021 Karlsruhe, Germany
c   Lehn Institute of Functional Materials (LIFM), School of Chemistry, Sun Yat-Sen University (SYSU), Guangzhou 510275, P. R. of China
› Author AffiliationsThe authors thank Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung (Swiss National Science Foundation) (SNF) (Grant No. 200020-178808) for continuous and generous financial support. M.M. acknowledges support from the 111 project (Grant No. 90002-18011002).
Further Information

Publication History

Received: 19 June 2019

Accepted after revision: 02 August 2019

Publication Date:
03 September 2019 (online)

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Abstract

Organosulfur compounds are ubiquitous in synthetic chemistry, biology and materials chemistry. The reactivity of free sulfhydryls requires their masking in many synthetic strategies. To facilitate the isolation of protected thiols by chromatography, we propose 2-(3-cyanopropyldimethylsilyl)ethyl as a polar protecting group analogue of 2-(trimethylsilyl)ethyl. The masked thiophenol is obtained in two synthetically complementing ways. Either an existing thiophenol is protected, or the protected thiol group is introduced by a cross-coupling reaction. In both cases the required reagents are readily available from inexpensive starting materials. Thiol protection and thiol introduction both tolerate a large variety of functional groups and substitution patterns, and the protected thiophenols are stable toward a broad range of reaction conditions. The stability of the protected derivatives in cross-coupling reactions and the mild reaction conditions for the release of the protecting group further emphasizes the potential of the methodology.

Key words

thiols - protecting groups - cross-coupling - easy to purify - polarity

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690184.
  • Supporting Information

Primary Data

    for this article are available online at https://doi.org/10.1055/s-0039-1690184 and can be cited using the following DOI: 10.4125/pd0107th.
  • Primary Data
 

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