Xu F.
Xiao X.
Hoye TR.
* University of Minnesota, Minneapolis, USA
Photochemical Hexadehydro-Diels–Alder Reaction.
J. Am. Chem. Soc. 2017;
139: 8400-8403
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.
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.
