Ligand-Promoted Borylation of C(sp3)H Bonds with Palladium(II) Catalysts

A quinoline‐based ligand effectively promotes the palladium‐catalyzed borylation of C(sp3)H bonds. Primary β‐C(sp3)H bonds in carboxylic acid derivatives as well as secondary C(sp3)H bonds in a variety of carbocyclic rings, including cyclopropanes, cyclobutanes, cyclopentanes, cyclohexanes, and c...

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Published in:Angewandte Chemie International Edition 2016-01, Vol.55 (2), p.785-789
Main Authors: He, Jian, Jiang, Heng, Takise, Ryosuke, Zhu, Ru-Yi, Chen, Gang, Dai, Hui-Xiong, Dhar, T. G. Murali, Shi, Jun, Zhang, Hao, Cheng, Peter T. W., Yu, Jin-Quan
Format: Article
Language:English
Subjects:
amino acids
Bonding
Boron Compounds - chemistry
borylation
Carboxylic acids
Catalysis
Catalysts
Chemical reactions
CH activation
Hydrogen Bonding
Iridium
Ligands
Organic compounds
Palladium
Palladium - chemistry
Quinoline
Rhodium
synthetic methods
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Summary:A quinoline‐based ligand effectively promotes the palladium‐catalyzed borylation of C(sp3)H bonds. Primary β‐C(sp3)H bonds in carboxylic acid derivatives as well as secondary C(sp3)H bonds in a variety of carbocyclic rings, including cyclopropanes, cyclobutanes, cyclopentanes, cyclohexanes, and cycloheptanes, can thus be borylated. This directed borylation method complements existing iridium(I)‐ and rhodium(I)‐catalyzed CH borylation reactions in terms of scope and operational conditions. A quinoline‐based ligand promotes the efficient palladium‐catalyzed borylation of primary β‐C(sp3)H bonds in carboxylic acid derivatives as well as secondary C(sp3)H bonds in a variety of carbocycles. This directed borylation method complements existing iridium(I)‐ and rhodium(I)‐catalyzed CH borylation reactions in terms of scope and reaction conditions.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201509996