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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

Contributor(s):
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
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Further Information

Publication History

Publication Date:
18 July 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.


 

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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