Brønsted acid-catalysed desilylative heterocyclisation to form substituted furans

Emily Babcock, Shafiq Rahman, James Taylor

Research output: Contribution to journalArticlepeer-review

1 Citation (SciVal)

Abstract

Heterocyclisation of tert-butyldimethylsilyl (TBS) protected γ-hydroxy-α,β-unsaturated ketones catalysed by para-toluenesulfonic acid (p-TSA) to form substituted furans is reported. The reaction proceeds under mild conditions at room temperature in methanol to give a range of furan products (21 examples, up to 98% yield). Mechanistic experiments suggest the reaction proceeds via in situ deprotection followed by catalytic dehydrative heterocyclisation.
Original languageEnglish
Pages (from-to)163-168
Number of pages6
JournalOrganic & Biomolecular Chemistry
Volume21
Issue number1
Early online date30 Nov 2022
DOIs
Publication statusPublished - 30 Nov 2022

Bibliographical note

Funding Information:
The authors thank the University of Bath (studentship to E. G. B) and the EPSRC (Grant code: EP/V051423/1) for funding. We thank a reviewer for insightful comments regarding the alternative reaction mechanisms.

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