Flash Chemistry Enables High Productivity Metalation-Substitution of 5-Alkyltetrazoles

Yuk Fung Wong, Christopher Thomson, Filipe Vilela, Graeme Barker

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)
25 Downloads (Pure)


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.

Original languageEnglish
Pages (from-to)13413-13424
Number of pages12
JournalChemical Science
Issue number40
Early online date15 Sept 2021
Publication statusPublished - 28 Oct 2021

ASJC Scopus subject areas

  • Chemistry (miscellaneous)
  • General Chemistry
  • Organic Chemistry


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