Alkyl and Aryl Thiol Addition to [1.1.1]Propellane: Scope and Limitations of a Fast Conjugation Reaction.
作者： Robin M. Bär , Stefan Kirschner , Martin Nieger , Stefan Bräse
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摘要: Herein we report the addition of different thiols to strained carbon-carbon bond [1.1.1]propellane (1). We investigated reaction pathway, performed with substituted thiols, hydrogen sulfide and protected cysteine verified further modifications products. The clean proceeds probably through a radical chain process as confirmed deuterium labelling experiments. It shows great functional group tolerance halogen-, hydroxy-, methoxy-, carboxy-, amino- nitro-substituted could be added 1 few by-products in 16-90% yield. Oxidation products offers tuning polarity subsequent reactions "click"-type even faster selenols show proof-of-concept. thiol facile tool for surface modifications, conjugations hydrophilicity bio- medicinal chemistry compounds.
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