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Synfacts 2017; 13(08): 0809
DOI: 10.1055/s-0036-1590716
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

The Power of Light in Hexadehydro-Diels–Alder Chemistry

Rezensent(en):
Timothy M. Swager
,
Cagatay Dengiz
Xu F. Xiao X. Hoye TR. * University of Minnesota, Minneapolis, USA
Photochemical Hexadehydro-Diels–Alder Reaction.

J. Am. Chem. Soc. 2017;
139: 8400-8403
CrossrefPubMedSuche in Google Scholar
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Publikationsverlauf

Publikationsdatum:
18. Juli 2017 (online)

 
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Key words

photochemistry - cycloisomerization - Diels–Alder reaction

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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