Direct Conversion of Internal Alkynes into -Iodoenones: One-Step Collaborative Iodination and Oxidation

The reaction of an internal alkyne with 2,6-dichloropyridine N-oxide, a nucleophilic oxidant, and electrophilic N-iodosuccinimide (NIS) simultaneously enables the direct access to versatile -iodoenones. Electronically biased internal alkynes undergo the one-step transformation with excellent regiose...

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Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 358; no. 9; pp. 1417 - 1420
Main Authors Wang, Youliang, Genoux, Alexandre, Ghorai, Subir, Chen, Hongyi, Todd, Robert, Zhang, Liming
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 28.04.2016
Wiley Subscription Services, Inc
Subjects
Alkynes
Catalysis
Chemistry
Chemistry, Applied
Chemistry, Organic
Direct conversion
Gold
Iodination
Oxidation
Physical Sciences
Science & Technology
iodination
pyridine N-oxides
ACIDS
alkynes
oxidation
ALPHA-IODOENONES
EFFICIENT SYNTHESIS
enones
HALOENONES
KETONES
PROPARGYLIC ALCOHOLS
OXO GOLD CARBENES
CYCLIZATION
CATALYSTS
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Summary:The reaction of an internal alkyne with 2,6-dichloropyridine N-oxide, a nucleophilic oxidant, and electrophilic N-iodosuccinimide (NIS) simultaneously enables the direct access to versatile -iodoenones. Electronically biased internal alkynes undergo the one-step transformation with excellent regioselectivities and with practical Z/E ratios. In comparison to the related oxidative gold catalysis using pyridine N-oxides, this reaction employs NIS as the stoichiometric ynophile instead of the soft acidic noble metal catalyst and affords products featuring an additional versatile CI bond. Similar strategies for replacing ynophilic cationic gold(I) complexes in oxidative gold catalysis with likewise ynophilic stoichiometric electrophiles would enable the development of new synthetic methods.
Bibliography:National Science Foundation
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201600027