Controllable Mono-/Dialkenylation of Benzyl Thioethers through Rh-Catalyzed Aryl CH Activation

Controllable Mono-/Dialkenylation of Benzyl Thioethers through Rh-Catalyzed Aryl CH Activation

Under solvent control: Benzyl thioethers were alkenylated in excellent yields with broad substrate scope and the selectivity (mono‐ vs. disubstituted product) was controlled by the solvent and ratio of reactants (see scheme). Sequential alkenylation with two different alkenes was also carried out in...

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Veröffentlicht in:Chemistry : a European journal 2013-09, Vol.19 (36), p.11898-11903
Hauptverfasser: Zhang, Xi-Sha, Zhu, Qi-Lei, Zhang, Yun-Fei, Li, Yan-Bang, Shi, Zhang-Jie
Format: Artikel
Sprache:eng
Schlagworte:
Activation
Alkenes
alkenylation
Aromatic compounds
Bonding
CH activation
Derivatives
Hydrogenation
rhodium
Solvents
thioethers
Toluene
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Zusammenfassung:Under solvent control: Benzyl thioethers were alkenylated in excellent yields with broad substrate scope and the selectivity (mono‐ vs. disubstituted product) was controlled by the solvent and ratio of reactants (see scheme). Sequential alkenylation with two different alkenes was also carried out in a one‐pot process. In addition, the thioether directing group was removed in a one‐pot process with simultaneous hydrogenation of the double bond to give the toluene derivatives.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201300829