Aryl phosphonates are important molecular building blocks in the development of pharmaceuticals, agrochemicals, and materials. There are numerous approaches to preparing phosphonates via C-P bond formation, mostly involving transition metal catalyzed coupling (e.g., Hirao coupling). This presentation describes our efforts to develop an approach to synthesizing aryl phosphonates using benzyne intermediates. We have found that <i>O</i>-silyl phosphites add to arynes and simultaneously form C-P and C-Si bonds, resulting in a 2-silyl aryl phosphonate product. This presentation will describe our efforts to fully evaluate the scope of structurally complex aryl phosphonates that can be formed by a sequential generation of benzynes under Abramov-aryne and fluoride-mediated elimination reactions.

Aryne-Abramov reaction for the synthesis of 2-silyl aryl phosphonates

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.