Brønsted acid-catalysed desilylative heterocyclisation to form substituted furans

Emily Babcock; Shafiq Rahman; James Taylor

doi:10.1039/D2OB01828D

Brønsted acid-catalysed desilylative heterocyclisation to form substituted furans

Emily Babcock, Shafiq Rahman, James Taylor

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

2 Citations (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 language	English
Pages (from-to)	163-168
Number of pages	6
Journal	Organic & Biomolecular Chemistry
Volume	21
Issue number	1
Early online date	30 Nov 2022
DOIs	https://doi.org/10.1039/D2OB01828D
Publication status	Published - 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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10.1039/D2OB01828DLicence: CC BY

Cite this

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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.",

author = "Emily Babcock and Shafiq Rahman and James Taylor",

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AU - Rahman, Shafiq

AU - Taylor, James

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N2 - 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.

AB - 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.

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JF - Organic & Biomolecular Chemistry

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ER -

Brønsted acid-catalysed desilylative heterocyclisation to form substituted furans

Abstract

Bibliographical note

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Boronic Acid-Catalysed Dehydrative Synthesis

Data for Brønsted Acid-Catalyzed Desilylative Heterocyclization to form Substituted Furans

Cite this

Brønsted acid-catalysed desilylative heterocyclisation to form substituted furans

Abstract

Bibliographical note

Access to Document

Other files and links

Fingerprint

Projects

Boronic Acid-Catalysed Dehydrative Synthesis

Datasets

Data for Brønsted Acid-Catalyzed Desilylative Heterocyclization to form Substituted Furans

Cite this