Triarylphosphines as Aryl Donors for Pd(II)-Catalyzed Aromatic Coupling of Oxabenzonorbornadienes

A new approach was developed for Pd­(II)-catalyzed aromatic coupling of oxabenzo­norbornadienes with triaryl­phosphines as both ligands and aryl donors. Diverse functional groups including halo- (F–, Cl–, and Br−), CF3-, and furyl groups are well tolerated. For unsymmetrical triarylphosphines, the m...

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Veröffentlicht in:Organic letters 2015-09, Vol.17 (18), p.4628-4631
Hauptverfasser: Zhou, Hui, Li, Jixing, Yang, Huameng, Xia, Chungu, Jiang, Gaoxi
Format: Artikel
Sprache:eng
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Zusammenfassung:A new approach was developed for Pd­(II)-catalyzed aromatic coupling of oxabenzo­norbornadienes with triaryl­phosphines as both ligands and aryl donors. Diverse functional groups including halo- (F–, Cl–, and Br−), CF3-, and furyl groups are well tolerated. For unsymmetrical triarylphosphines, the migration ability of aryls is consistent with the electronic property of substituents and maintains the order EDG–Ar > H–Ar > EWD–Ar (EDG means electron-donating group, EWG means electron-withdrawing group). A preliminary mechanistic study was also disclosed.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b02366