Ethanol as a Hydrogenating Agent: Palladium‐Catalyzed Stereoselective Hydrogenation of Ynamides To Give Enamides

Ethanol is shown to act as a hydrogenating agent for ynamides under palladium catalysis. This behavior is different from the normally expected reaction of ethanol addition to alkynes. The reaction shows stereoselectivity for E enamides, which is in contrast to reports using other hydrogenating sourc...

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Vydáno v:Angewandte Chemie International Edition Ročník 56; číslo 24; s. 6984 - 6988
Hlavní autoři: Reddy, Alla Siva, Swamy, K. C. Kumara
Médium: Journal Article
Jazyk:angličtina
Vydáno: WEINHEIM Wiley 06.06.2017
Wiley Subscription Services, Inc
Vydání:International ed. in English
Témata:
Alkynes
Ammonium
Catalysis
Chemistry
Chemistry, Multidisciplinary
Deuterium
enamides
Ethanol
Hydrogenation
Palladium
Physical Sciences
Science & Technology
Stereoselectivity
ynamides
FUNCTIONALIZED YNAMIDES
HYDROGENOLYSIS
GOLD CATALYSIS
enamides
ACIDS
REACTIVITY
ethanol
hydrogenation
SELECTIVE SEMIHYDROGENATION
REDUCTION
palladium
ynamides
2+2+2 CYCLOADDITIONS
TANDEM-CYCLIZATION
ALKYNE SEMIHYDROGENATION
ISSN:1433-7851, 1521-3773, 1521-3773
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Shrnutí:Ethanol is shown to act as a hydrogenating agent for ynamides under palladium catalysis. This behavior is different from the normally expected reaction of ethanol addition to alkynes. The reaction shows stereoselectivity for E enamides, which is in contrast to reports using other hydrogenating sources. The method was also extended to ynamines. Alternatively, the use of ethanol and ammonium formate as the hydrogenating source gives Z enamides. The role of ethanol in hydrogenation was demonstrated by means deuterium labeling experiment. One for the road: Ethanol acts as a hydrogenating agent for ynamides under palladium catalysis. This behavior is different from the normally expected addition of ethanol to alkynes. The reactions show stereoselectivity for E enamides, which is in contrast to reports using other hydrogenating sources, and the method was also extended to ynamines. Alternatively, the use of ethanol/ammonium formate as the hydrogenating source gives Z enamides.
Bibliografie:ObjectType-Article-1
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ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.201702277