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Controllable Mono‐/Dialkenylation of Benzyl Thioethers through Rh‐Catalyzed Aryl CH Activation
Author(s) -
Zhang XiSha,
Zhu QiLei,
Zhang YunFei,
Li YanBang,
Shi ZhangJie
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201300829
Subject(s) - thioether , toluene , catalysis , aryl , substrate (aquarium) , selectivity , solvent , chemistry , organic chemistry , medicinal chemistry , combinatorial chemistry , scope (computer science) , computer science , programming language , alkyl , oceanography , geology
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.