The (ongoing) evolution of the hexadehydro-Diels-Alder (HDDA) reaction

1 November 2017

Chemistry Department Seminar: Thomas R. Hoye 

Department of Chemistry, University of Minnesota
Friday, November 3, 2017

3:30 – 4:30 pm / Old Music Hall 103

Official/Unofficial story

Since mid-2011 researchers in our laboratories have been developing a process that we call the hexadehydro-Diels–Alder (HDDA) reaction. This net [4+2] cycloisomerization produces an o-benzyne derivative, which is then rapidly captured in a subsequent trapping event. The HDDA reaction is a rare example of a transformation that generates a high-energy, reactive intermediate by way of a highly exothermic (ca. –50 kcal•mol-1) reaction! This two-stage benzyne generation-trapping cascade results in the rapid assembly of structurally complex benzenoid products. This chemistry is both preparatively valuable and mechanistically enlightening. Fundamentally new modes of benzyne reactivity have been uncovered. I will discuss these developments from the perspective of their fundamental mechanistic and energetic features and synthetic utility.

The Hexadehydro-Diels–Alder (HDDA) Cascade

  Cascade THoye

In this lecture I will emphasize some of the more recent aspects of our studies

These may include:

• three-component reactions
• natural product synthesis
• natural product derivatization reactions
• the photochemical HDDA reaction
• the discovery of new organic light-emitting diode (OLED) materials
• the pentadehydro-Diels-Alder reaction
• the domino HDDA reaction