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Updated: Aug 6, 2026

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
Published on: April 9, 2018
Solid phase approaches to N-heterocycles using a sulfur linker cleaved by SmI2
Laura A McAllister1, Kristy L Turner, Stephen Brand
1Department of Chemistry, Joseph Black Building, University of Glasgow, Glasgow, G12 8QQ, UK.
Abstract:
A sulfur HASC (alpha-hetero-atom substituted carbonyl) linker has been utilized in solid-phase approaches to oxindoles and tetrahydroquinolones. The route to oxindoles employs the first Pummerer cyclizations on solid phase, whereas the route to tetrahydroquinolones involves a microwave-assisted Heck reaction followed by a Michael cyclization. In both cases, the linker is cleaved in a traceless fashion by electron transfer from samarium(II) iodide. The routes illustrate the compatibility of the linker system with a number of reaction types and its utility for library synthesis.
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