Regioselective and Diastereodivergent Gold-Catalyzed Propargylation of Synergistically Activated Chromones
In this work, we report the use of propargylsilanes in a gold-catalyzed regio and distereoselective propargylation of chromones synergistically activated by in situ generated TMS+, using a picolinate gold complex as catalyst. A diastereodivergence is observed compared with the analogous reaction using a phosphite ligand for the gold catalyst. Formation of the major diastereoisomer is supported by a density functional theory (DFT) computational analysis of the mechanistic pathway, indicating kinetic control of the reaction selectivity.
Authors
- Javier Santamarı́a (ORCID: https://orcid.org/0000-0001-6369-4183)
- Ignacio Funes‐Ardoiz (ORCID: https://orcid.org/0000-0002-5843-9660)
- Diego Sampedro (ORCID: https://orcid.org/0000-0003-2772-6453)
- Sergio Fernández (ORCID: https://orcid.org/0000-0002-2955-6550)
- Julio Álvarez-Valle (ORCID: https://orcid.org/0000-0002-8659-5003)
- Cecilia Merino‐Robledillo
Institutions
- Universidad de Oviedo (ES)
- Universidad de La Rioja (ES)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2026-10-30
- DOI
- https://doi.org/10.1021/acs.joc.6c02113
- Primary Topic
- Catalytic Alkyne Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Ministerio de Ciencia, Innovación y Universidades
- Ministerio de Ciencia e Innovación
- Universidad de Oviedo
- Universidad de La Rioja
- European Regional Development Fund
- Agencia Estatal de Investigación