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Published on: August 19, 2012
Photocatalytic Radical Azido/Fluorosulfonylation of Unactivated Alkenes: Accessing Hubs Bridging CuAAC and SuFEx
Guanhua Pei1,2, Peng Wang3, Lu Lin1
1State Key Laboratory of Physical Chemistry of Solid Surfaces, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China.
Abstract:
Herein, we describe the successful development of an azido-fluorosulfonylation reaction of alkenes under photoredox catalysis, which could allow the installation of the two "clickable" groups, -N3 and -SO2F, on a C-C double bond, with TMSN3 as the azide source. The utilization of the difunctionalization products is also demonstrated in the construction of a library of 1,2,3-triazolesulfonyl fluoride compounds as well as drug molecule ligation by merging copper-catalyzed azide-alkyne cycloaddition (CuAAC) and sulfur(VI) fluoride exchange (SuFEx), the two generations of click reactions. Mechanistic studies suggest a radical fluorosulfonylation/azidation mechanism and unveil FSO2N3 as a new and potential fluorosulfonyl radical precursor.
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