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Synthesis 2019; 51(22): 4153-4164
DOI: 10.1055/s-0039-1690184
DOI: 10.1055/s-0039-1690184
paper
2-(3-Cyanopropyldimethylsilyl)ethyl as a Polar Sulfur Protecting Group
The 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)
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.
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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