Tetrazoles play a prominent role in medicinal chemistry due to their role as carboxylate bioisosteres but have largely been overlooked as C-H functionalisation substrates. We herein report the development of a high-yielding and general procedure for the heterobenzylic C-H functionalisation of 5-alkyltetrazoles in up to 97% yield under batch conditions using a metalation/electrophilic trapping strategy. Through the use of thermal imaging to identify potentially unsafe exotherms, a continuous flow procedure using a flash chemistry strategy has also been developed, allowing products to be accessed in up to 95% yield. This enabled an extremely high productivity rate of 141 g h −1to be achieved on an entry-level flow system.
|Number of pages||12|
|Early online date||15 Sept 2021|
|Publication status||Published - 28 Oct 2021|
ASJC Scopus subject areas
- Chemistry (miscellaneous)
- Organic Chemistry