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

Bannwart, Linda M. and Rieder, Pascal S. and Mayor, Marcel. (2019) 2-(3-Cyanopropyldimethylsilyl)ethyl as a Polar Sulfur Protecting Group. Synthesis, 51 (22). pp. 4153-4164.

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Official URL: https://edoc.unibas.ch/75501/

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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.
Faculties and Departments:05 Faculty of Science > Departement Chemie > Chemie > Molecular Devices and Materials (Mayor)
UniBasel Contributors:Mayor, Marcel and Bannwart, Linda Maria and Rieder, Pascal
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:Georg Thieme
ISSN:0039-7881
e-ISSN:1437-210X
Note:Publication type according to Uni Basel Research Database: Journal article
Identification Number:
Last Modified:21 Feb 2020 11:56
Deposited On:21 Feb 2020 11:56

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