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Synfacts 2017; 13(08): 0809
DOI: 10.1055/s-0036-1590716
DOI: 10.1055/s-0036-1590716
Synthesis of Materials and Unnatural Products
The Power of Light in Hexadehydro-Diels–Alder Chemistry
Further Information
Publication History
Publication Date:
18 July 2017 (online)
Significance
The authors demonstrate the efficient formation of reactive benzyne intermediates through photochemically initiated hexadehydro-Diels–Alder (HDDA) cycloisomerization reaction of multi-yne precursors. The reported photochemical transformation occurs at lower temperatures than the thermal version of the HDDA.
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Comment
The authors also report that the resulting benzyne intermediates behave identically to those obtained through thermal HDDA reactions. The subsequent, highly efficient trapping reactions with π-donors and nucleophilic agents demonstrate the application of this method to access more elaborate structures.
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