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Trifluoromethylthiolation of Aryl Iodides and Bromides Enabled by a Bench‐Stable and Easy‐To‐Recover Dinuclear Palladium(I) Catalyst
Author(s) -
Yin Guoyin,
Kalvet Indrek,
Schoenebeck Franziska
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201501617
Subject(s) - palladium , aryl , catalysis , chemistry , dimer , combinatorial chemistry , coupling reaction , organic chemistry , alkyl
While palladium catalysis is ubiquitous in modern chemical research, the recovery of the active transition‐metal complex under routine laboratory applications is frequently challenging. Described herein is the concept of alternative cross‐coupling cycles with a more robust (air‐, moisture‐, and thermally‐stable) dinuclear Pd I complex, thus avoiding the handling of sensitive Pd 0 species or ligands. Highly efficient CSCF 3 coupling of a range of aryl iodides and bromides was achieved, and the recovery of the Pd I complex was accomplished via simple open‐atmosphere column chromatography. Kinetic and computational data support the feasibility of dinuclear Pd I catalysis. A novel SCF 3 ‐bridged Pd I dimer was isolated, characterized by X‐ray crystallography, and verified to be a competent catalytic intermediate.