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Unlocking Migratory Insertion in Gold Redox Catalysis
Ist Teil von
Angewandte Chemie International Edition, 2023-07, Vol.62 (29), p.e202304019-n/a
Auflage
International ed. in English
Ort / Verlag
Germany: Wiley Subscription Services, Inc
Erscheinungsjahr
2023
Link zum Volltext
Quelle
Alma/SFX Local Collection
Beschreibungen/Notizen
Exploration of elementary reactions in organometallic catalysis is an important method with which to discover new reactions. In this article, we report a gold(I)‐catalyzed iodo‐alkynylation of benzyne involving the merging of challenging migratory insertion and an oxidative addition process in gold catalytic cycle. A wide range of structurally diverse alkynyl iodides are good coupling partners in this iodo‐alkynylation transformation. Both aliphatic and aromatic alkynyl iodides can react with benzynes smoothly to afford highly functionalized 1,2‐disubstituted aromatics in moderate to good yields. Its good functional group compatibility and late‐stage application of complex molecules demonstrate its synthetic robustness. Studies of the mechanism reveals the feasibility of oxidative addition and the DFT calculations demonstrate the possible migratory insertion of benzyne into AuIII‐carbon bonds in the AuI/AuIII redox catalytic cycle, representing an important step towards an elementary reaction in gold chemistry research.
A gold(I)‐catalyzed iodo‐alkynylation of benzyne involving the merging of challenging migratory insertion and an oxidative addition process in the AuI/AuIII catalytic cycle has been reported. It represents important progress within the field of gold redox couple chemistry and in particular in the migratory insertion topic.