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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Veröffentlicht in:Angewandte Chemie International Edition Jg. 56; H. 24; S. 6984 - 6988
Hauptverfasser: Reddy, Alla Siva, Swamy, K. C. Kumara
Format: Journal Article
Sprache:Englisch
Veröffentlicht: WEINHEIM Wiley 06.06.2017
Wiley Subscription Services, Inc
Ausgabe:International ed. in English
Schlagworte:
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
Online-Zugang:Volltext
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Abstract 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.
AbstractList 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.
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.
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.
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 Eenamides, 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 Zenamides. The role of ethanol in hydrogenation was demonstrated by means deuterium labeling experiment.
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.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.
Author Siva Reddy, Alla
Kumara Swamy, K. C.
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  fullname: Swamy, K. C. Kumara
  email: kckssc@uohyd.ac.in
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Issue 24
Keywords FUNCTIONALIZED YNAMIDES
HYDROGENOLYSIS
GOLD CATALYSIS
enamides
ACIDS
REACTIVITY
ethanol
hydrogenation
SELECTIVE SEMIHYDROGENATION
REDUCTION
palladium
ynamides
2+2+2 CYCLOADDITIONS
TANDEM-CYCLIZATION
ALKYNE SEMIHYDROGENATION
Language English
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Snippet Ethanol is shown to act as a hydrogenating agent for ynamides under palladium catalysis. This behavior is different from the normally expected reaction of...
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SubjectTerms Alkynes
Ammonium
Catalysis
Chemistry
Chemistry, Multidisciplinary
Deuterium
enamides
Ethanol
Hydrogenation
Palladium
Physical Sciences
Science & Technology
Stereoselectivity
ynamides
Title Ethanol as a Hydrogenating Agent: Palladium‐Catalyzed Stereoselective Hydrogenation of Ynamides To Give Enamides
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.201702277
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https://www.ncbi.nlm.nih.gov/pubmed/28471083
https://www.proquest.com/docview/1904135760
https://www.proquest.com/docview/1895278230
Volume 56
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