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 inJournal of the American Chemical Society Vol. 140; no. 50; pp. 17439 - 17443
Main Authors Li, Ting, Zhang, Liming
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.12.2018
Amer Chemical Soc
Subjects
Aldehydes - chemistry
Alkynes - chemistry
carbon-hydrogen bond activation
Catalysis
catalytic activity
Chemistry
Chemistry, Multidisciplinary
Coordination Complexes - chemistry
Cyclization
Furans - chemical synthesis
gold
Gold - chemistry
Isomerism
Lewis bases
Ligands
Organosilicon Compounds - chemistry
phosphine
Phosphines - chemistry
Physical Sciences
Science & Technology
ISOMERIZATIONS
ALKYNES
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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.
Bibliography:NIH RePORTER
ObjectType-Article-1
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ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.8b12478