Bifunctional Biphenyl-2-ylphosphine Ligand Enables Tandem Gold-Catalyzed Propargylation of Aldehyde and Unexpected Cycloisomerization

Despite extensive studies in gold catalysis, σ-allenylgold species have not been invoked as catalytic intermediates and their reactivities not studied. This work reports for the first time they are generated in situ and undergo nucleophilic addition to activated aldehydes in a bifunctional phosphine...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2018-12, Vol.140 (50), p.17439-17443
Main Authors: Li, Ting, Zhang, Liming
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
Alkynes - chemistry
Catalysis
Coordination Complexes - chemistry
Cyclization
Furans - chemical synthesis
Gold - chemistry
Isomerism
Ligands
Organosilicon Compounds - chemistry
Phosphines - chemistry
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Summary:Despite extensive studies in gold catalysis, σ-allenylgold species have not been invoked as catalytic intermediates and their reactivities not studied. This work reports for the first time they are generated in situ and undergo nucleophilic addition to activated aldehydes in a bifunctional phosphine ligand-enabled gold catalysis. This development reveals a broad range of opportunities to achieve propargylic C–H functionalization for the first time under catalytic and mild conditions. The homopropargylic alcohols generated undergo ligand-enabled cycloisomerizations involving an unexpected silyl migration.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.8b12478