Chemistry Events

See a list of this year’s seminar speakers, along with summaries of past seminars, on the Chemistry Department Seminars page.

Feb 28

Chemistry Department Seminar: Jenny Martinez (Yale)

presents "Exploiting the Reactivity of Dienes via Electrophilic Addition with Anionic and Radical Intermediates"

Friday, February 28th, 2020
3:30 – 4:30 pm / Evelyn M. Anderson Hall 329
Jenny Martinez poster
Jenny Martinez

To this day, countless chemical transformations are known for the functionalization of the α- and β-positions of cyclic ketones. However, few methods are known for functionalization at the γ-position of cycloalkanes. To answer the question of direct functionalization at the γ-position of cycloalkanones, stabilized dienolate intermediates in both anionic and radical conditions have been extensively studied. These reactive intermediates have opened a wide array of product possibilities upon exposure to a series of diverse reaction partners. Through these methods, reaction conditions have been discovered for the formation of new carbon–halogen bonds, carbon–oxygen and carbon–carbon bonds selectively at the γ-position of enones and related systems. Additionally, the reactivity of dienes in pyrrole systems has also been examined. As a result, a protocol to access new sterically demanding halopyridines via the Ciamician–Dennstedt rearrangement has been discovered. Furthermore, an economical and efficient synthesis of 2,6-di-t-butylpyridine analogues was also accomplished.

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