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Palladium-Catalyzed Carbonylation of Aryl Iodides with Sulfinamides
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry.ORCID iD: 0000-0002-6257-4064
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry.
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry.
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry.
2015 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 32, 7069-7074 p.Article in journal (Refereed) Published
Abstract [en]

A facile palladium(0)-catalyzed carbonylative protocol for the generation of new acyl-sulfinamides in moderate to good yields is described. Aliphatic and aromatic sulfinamides were exploited as hitherto unexplored nucleophiles in carbonylation chemistry, with use of CO gas generated ex situ from Mo(CO)6 in a sealed two-chamber system. Both electron-poor and electron-rich (hetero)aryl iodides were employed as electrophiles. The two-chamber system and the use of an inorganic base were essential for efficacious synthesis of acyl-sulfinamide products. Finally, it was demonstrated that a one-pot (or single-vial) synthesis of acyl-sulfinamides was feasible under CO at balloon pressure in the presence of Cs2CO3 as base.

Place, publisher, year, edition, pages
2015. no 32, 7069-7074 p.
Keyword [en]
Homogenous catalysis; Carbonylation; Palladium; Molybdenum; Sulfinamides
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-265231DOI: 10.1002/ejoc.201500875ISI: 000364532000012OAI: oai:DiVA.org:uu-265231DiVA: diva2:864142
Available from: 2015-10-26 Created: 2015-10-26 Last updated: 2017-12-01Bibliographically approved

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Belfrage, Anna KarinLarhed, MatsSandström, Anja

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