Cu‐Catalyzed Intramolecular Borylation‐Cross Coupling Reaction of Unactivated Alkenes to Borylated Indolines

Cu‐catalyzed intramolecular borylation‐cross coupling reaction of alkenes was developed. Racemic and chiral borylated indolines were achieved by borylation‐cross coupling of alkenes with B2pin2 via simultaneous construction of C−C and C−B bonds by Cu/phosphine ligand system. With CuOAc and DPPE liga...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2023-12, Vol.365 (23), p.4227-4232
Main Authors: Fan, Lin, Yan, Xinlong, Li, Changjiang, Cao, Yuxue, Liu, Guodu
Format: Article
Language:English
Subjects:
3-Substituted Borylated Indolines
Alkenes
B2pin2
Chemical reactions
Copper
Cross coupling
Heterocyclic compounds
Intramolecular Borylation-Cross Coupling Reaction
Ligands
Phosphines
Substitutes
Synthesis
Unactivated Alkenes
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Summary:Cu‐catalyzed intramolecular borylation‐cross coupling reaction of alkenes was developed. Racemic and chiral borylated indolines were achieved by borylation‐cross coupling of alkenes with B2pin2 via simultaneous construction of C−C and C−B bonds by Cu/phosphine ligand system. With CuOAc and DPPE ligand, a series of 3‐substituted borylated indoline derivatives were concisely synthesized in good to excellent yields in short time under mild conditions. Asymmetric synthesis was investigated by ligand screening, and the chiral 3‐substituted borylated indoline was obtained in 80% yield and 80:20 er with (R, R)‐Me‐Duphos. Application of 3‐substituted borylated indolines has been demonstrated by a gram scale synthesis and further functionalization.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202300888