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Site‐Selective, Modular Diversification of Polyhalogenated Aryl Fluorosulfates (ArOSO 2 F) Enabled by an Air‐Stable Pd I Dimer
Author(s) -
Mendel Marvin,
Kalvet Indrek,
Hupperich Daniel,
Magnin Guillaume,
Schoenebeck Franziska
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201911465
Subject(s) - aryl , linker , chemistry , dimer , context (archaeology) , trifluoromethanesulfonate , combinatorial chemistry , moiety , substrate (aquarium) , stereochemistry , organic chemistry , catalysis , computer science , paleontology , alkyl , oceanography , biology , geology , operating system
Since 2014, the interest in aryl fluorosulfates (ArOSO 2 F) as well as their implementation in powerful applications has continuously grown. In this context, the enabling capability of ArOSO 2 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−OSO 2 F, C−Br, and C−Cl sites, which makes it possible to diversify the arene in the presence of OSO 2 F or utilize OSO 2 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 Pd I dimer.