Selective Palladium‐Catalyzed Domino Heck/Buchwald–Hartwig Arylations of N‐Glycosylcinnamamides: An Efficient Route to 4‐Aryl‐N‐glycosylquinolin‐2‐ones

An efficient and selective domino Heck/Buchwald–Hartwig arylations of readily available N‐glycosylcinnamamides with aryl iodides have been established. Using palladium(II) acetate as a catalyst, potassium acetate as the base and tetrabutylamonium bromide as an additive in dioxane, the protocol prove...

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Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 359; no. 8; pp. 1320 - 1330
Main Authors Luong, Thi Thanh Huyen, Touchet, Sabrina, Alami, Mouad, Messaoudi, Samir
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 17.04.2017
Wiley Subscription Services, Inc
Wiley-VCH Verlag
Subjects
4-aryl-N-glycosylquinolin-2-ones
Acetates
Additives
Aromatic compounds
Bromides
Catalysis
Catalysts
Chemical Sciences
Chemistry
Chemistry, Applied
Chemistry, Organic
Heck/Buchwald–Hartwig reactions
Iodides
N-glycosylcinnamamides
Organic chemistry
Palladium
palladium catalysis
Physical Sciences
Potassium
Science & Technology
Selectivity
Synthesis (chemistry)
palladium catalysis
TANDEM CATALYSIS
Heck/Buchwald-Hartwig reactions
SERIES
ACID
C-N
4-aryl-N-glycosylquinolin-2-ones
BEARING
N-glycosylcinnamamides
BIOAVAILABILITY
BIRDS
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Summary:An efficient and selective domino Heck/Buchwald–Hartwig arylations of readily available N‐glycosylcinnamamides with aryl iodides have been established. Using palladium(II) acetate as a catalyst, potassium acetate as the base and tetrabutylamonium bromide as an additive in dioxane, the protocol proved to be general, and a variety of 4‐aryl‐N‐glycosylquinolin‐2‐ones has been prepared in good yields with exclusive α‐ or β‐selectivity.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201601382