Stereoconvergent Synthesis of Z-1,3-Disubstituted-1,3-Dienes by Uphill Photocatalysis |
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| Authors: | Prof Steven T Diver Elise Glickert Laurence N Rohde Jr Thérèse Wild |
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| Institution: | Department of Chemistry, University at Buffalo, the State University of New York, 572 Natural Sciences Complex, Amherst, NY, 14260-3000 USA |
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| Abstract: | A variety of 1-aryl-1,3-dienes were isomerized from E to Z isomers by photocatalysis using Ru(bpy)3PF6]2 and blue LED light. Enrichment of the Z-isomer is thought to occur by selective triplet energy transfer from the photocatalyst to the stereoisomeric mixture. The 1,3-diene starting materials are easily made by catalytic ene-yne metathesis (EYM). To access 1,3-diene Z-stereoisomers directly, a one pot procedure was developed. Additional 1,3-dienes were investigated for both isomerization and Z-enrichment. The combination of cross EYM with photocatalysis allows for the stereoconvergent synthesis of Z-1,3-dienes. |
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| Keywords: | ene-yne metathesis Grubbs catalyst isomerization photocatalysis sensitizer |
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