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Site-Selective, Modular Diversification of Polyhalogenated Aryl Fluorosulfates (ArOSO2 F) Enabled by an Air-Stable PdI Dimer.

ABSTRACT: Since 2014, the interest in aryl fluorosulfates (ArOSO2 F) as well as their implementation in powerful applications has continuously grown. In this context, the enabling capability of ArOSO2 F will strongly depend on the substitution pattern of the arene, which ultimately dictates its overall function as drug candidate, material, or bio-linker. This report showcases the modular, substrate-independent, and fully predictable, selective functionalization of polysubstituted arenes bearing C-OSO2 F, C-Br, and C-Cl sites, which makes it possible to diversify the arene in the presence of OSO2 F or utilize OSO2 F as a triflate surrogate. Sequential and triply selective arylations and alkylations were realized within minutes at room temperature, using a single and air-stable PdI dimer.

SUBMITTER: Mendel M

PROVIDER: S-EPMC7003813 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature

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Site-Selective, Modular Diversification of Polyhalogenated Aryl Fluorosulfates (ArOSO2 F) Enabled by an Air-Stable PdI Dimer.

Mendel Marvin M Kalvet Indrek I Hupperich Daniel D Magnin Guillaume G Schoenebeck Franziska F

Angewandte Chemie (International ed. in English) 20191216 5

Since 2014, the interest in aryl fluorosulfates (ArOSO2 F) as well as their implementation in powerful applications has continuously grown. In this context, the enabling capability of ArOSO2 F will strongly depend on the substitution pattern of the arene, which ultimately dictates its overall function as drug candidate, material, or bio-linker. This report showcases the modular, substrate-independent, and fully predictable, selective functionalization of polysubstituted are ...[more]

PMID: 31733009

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