Gold()- and rhodium()-catalyzed formal regiodivergent C-H alkynylation of 1-arylpyrazolones

Formal regiodivergent C-H alkynylation of 1-aryl-5-pyrazolones has been realized under the catalysis of Rh( iii ) and Au( i ) complexes by using a hypervalent iodine reagent as the alkyne source. Mechanistic studies indicate that the regioselectivity is ascribed to not only the choice of the catalys...

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Published inOrganic & biomolecular chemistry Vol. 16; no. 16; pp. 286 - 2864
Main Authors Wang, Xueli, Li, Xingwei, Zhang, Yao, Xia, Lixin
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 2018
Royal Society of Chemistry
Subjects
Alkynes
Aromatic compounds
Catalysis
Chemistry
Chemistry, Organic
Functional groups
Gold
Iodine
Physical Sciences
Pyrazolones
Reagents
Regioselectivity
Rhodium
Science & Technology
Substrates
CATALYZED DIRECT ALKYNYLATION
DIRECTING GROUPS
FUNCTIONALIZATION
CHELATION-ASSISTANCE
ACTIVATION
MILD CONDITIONS
RH(III)
ARENES
DERIVATIVES
INDOLES
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Summary:Formal regiodivergent C-H alkynylation of 1-aryl-5-pyrazolones has been realized under the catalysis of Rh( iii ) and Au( i ) complexes by using a hypervalent iodine reagent as the alkyne source. Mechanistic studies indicate that the regioselectivity is ascribed to not only the choice of the catalyst but also the nature of the substrate. The substrate scope and functional group compatibility have been fully examined. A transition-metal-catalyzed formal regiodivergent C-H alkynylation of 1-aryl-5-pyrazolones is described.
Bibliography:Electronic supplementary information (ESI) available. See DOI
10.1039/c8ob00585k
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SourceType-Scholarly Journals-1
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ISSN:1477-0520
1477-0539
1477-0539
DOI:10.1039/c8ob00585k