A General Approach for the Generation of alpha-Thioalkyl Radicals from Pinacol Boronic Ester Precursors
A straightforward and effective method to produce alpha-thioalkyl radicals using stable and readily accessible pinacol boronic ester precursors is described. The generation of alpha-thioalkyl radicals proceeds via in-situ transesterification with MeOBcat or 3-methoxycatechol (MOC), and subsequent nucleohomolytic substitution at the boron atom with an oxygen-centred radical. The alpha-thioalkyl radicals can be trapped intermolecularly using a variety of conjugated enones and sulfonyl-based radical traps or subjected to intramolecular cyclisation.
Authors
- Philippe Renaud (ORCID: https://orcid.org/0000-0002-9069-7109)
- F. Dénès (ORCID: https://orcid.org/0000-0002-9791-3177)
- Lise Benoist (ORCID: https://orcid.org/0009-0008-0458-0651)
Institutions
- University of Bern (CH)
- Centre National de la Recherche Scientifique (FR)
- Chimie et Interdisciplinarité, Synthèse, Analyse, Modélisation (FR)
- Nantes Université (FR)
Publication Details
- Journal
- ChemRxiv
- Published
- 2026-10-29
- DOI
- https://doi.org/10.26434/chemrxiv.15011231/v1
- Primary Topic
- Radical Photochemical Reactions
- Type
- preprint