Construction of Bulky Ligand Libraries by Ru(II)-Catalyzed P(III)-Assisted ortho-C–H Secondary Alkylation

Modification of commercially available biaryl monophosphine ligands via ruthenium(II)-catalyzed P(III)-directed-catalyzed ortho C–H secondary alkylation is described. The use of highly ring-strained norbornene as a secondary alkylating reagent is the key to this transformation. A series of highly bu...

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Bibliographic Details
Published in:Journal of organic chemistry 2021-09, Vol.86 (17), p.11915-11925
Main Authors: Li, Ming, Tao, Jun-Yang, Wang, Liang-Neng, Li, Jia-Wei, Liu, Yue-Jin, Zeng, Ming-Hua
Format: Article
Language:English
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Summary:Modification of commercially available biaryl monophosphine ligands via ruthenium(II)-catalyzed P(III)-directed-catalyzed ortho C–H secondary alkylation is described. The use of highly ring-strained norbornene as a secondary alkylating reagent is the key to this transformation. A series of highly bulky ligands with a norbornyl group were obtained in excellent yields. The modified ligands with secondary alkyl group outperformed common substituted phosphines in the Suzuki–Miyaura cross-coupling reaction at a ppm mole level of Pd catalyst.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c01329