Metal-free tandem rearrangement/lactonization: Access to 3,3-disubstituted benzofuran-2-(3H)-ones

Santi, Micol, Ould, Darren M. C., Wenz, Jan, Soltani, Yashar, Melen, Rebecca L. ORCID: https://orcid.org/0000-0003-3142-2831 and Wirth, Thomas ORCID: https://orcid.org/0000-0002-8990-0667 2019. Metal-free tandem rearrangement/lactonization: Access to 3,3-disubstituted benzofuran-2-(3H)-ones. Angewandte Chemie International Edition 58 (23) , pp. 7861-7865. 10.1002/anie.201902985

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Abstract

A novel metal‐free synthesis of 3,3‐disubstituted benzofuran‐2(3H)‐ones from the reaction between α‐aryl‐α‐diazoacetates and triarylboranes is presented. Initially, triarylboranes were successfully investigated in α‐arylations of α‐diazoacetates, however in the presence of an ortho‐heteroatom substituent the boron enolate intermediate undergoes an intramolecular rearrangement to form a quaternary center. The intermediate cyclizes affording valuable 3,3‐disubstituted benzofuranones in good yields

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Schools > Chemistry
Publisher:	Wiley
ISSN:	1433-7851
Date of First Compliant Deposit:	8 April 2019
Date of Acceptance:	21 March 2019
Last Modified:	18 Nov 2024 06:00
URI:	https://orca.cardiff.ac.uk/id/eprint/121608

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