Journal
ORGANIC LETTERS
Volume 22, Issue 16, Pages 6473-6478Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c02281
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Funding
- Ministerio de Economia, Industria y Competitividad (MINECO/FEDER, UE) [CTQ2015-66954-P]
- Ministerio de Economia, Industria y Competitividad (FEDER/Ministerio de Ciencia, Innovacion y Universidades Agencia Estatal de Investigacion/Proyecto) [PGC2018-098660-B-I00]
- MECD
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A general catalytic anti-hydroarylation of electron-deficient internal alkynes compatible with both electron-poor and electron-rich aryl reagents is reported. This selectivity is achieved through a sequential syn-carbopalladation of the alkyne by an Ar-Pd species, followed by a tandem, Ir-photocatalyzed, counter-thermodynamic E -> Z isomerization. The use of ortho-substituted boronic acids enables direct access to pharmaceutically relevant heterocyclic cores via a cascade process. Mechanistic insight into the involvement of Ar-Pd versus Pd-H as an active species is provided.
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