Sulfur-based traceless linkers

Gayo KM, Suto MJ. Traceless linker Oxidative activation and displacement of a sulfur-based linker. Tetrahedron Lett 1997 38 211-214. 

Gayo, L. M. Suto, M. J. Traceless Linker Oxidative Activation and Displacement of a Sulfur-Based Linker, Tetrahedron Lett. 1997, 38, 211. 

Wagner and coworkers developed a traceless sulfur-based linker by applying the chemistry of benzylsulfonium salts [90]. Various benzyl bromides were attached to a thiol linker synthesized in four steps starting from Merrifield resin. Reaction of the resulting resin 96 with triethyloxonium tetrafluoroborate gave the solid supported sulfonium salt 97, which could be cleaved by reaction with boronic acids to afford biphenylmethyl derivatives 98 (Scheme 16.23). The alkylation can be regarded as an activation step and the linker as a safety-catch system. 

Sulfur-based linker units have been developed that utilize the reactivity of sulfur in a multitude of different forms and oxidation states. i ° The simplest linker units are the thioether-based linkers, and initially conditions for traceless cleavage of aliphatic... 

The development of suitable linkers is a continuous area of interest in solid-supported synthesis. Based on their previously explored traceless linking strategy using HASC (a-heteroatom-substituted carbonyl) linkers employing Smb, Procter and coworkers have demonstrated the use of a novel sulfur-based linker for the synthesis of the tetra-... 

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