Abstract
A protocol for the stereocontrolled synthesis of (E)- and (Z)-β,γ-unsaturated esters and amides is reported. 2-Chloroacetates as well as secondary and tertiary 2-chloroacetamides were successfully employed as electrophiles in the Suzuki-Miyaura cross-coupling reaction with potassium (E)- and (Z)-alkenyltrifluoroborates, affording the corresponding products in high yield.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
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Acetamides / chemistry*
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Alkenes / chemical synthesis*
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Alkenes / chemistry
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Borates / chemical synthesis*
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Borates / chemistry*
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Catalysis
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Chloroacetates / chemistry*
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Hydrocarbons, Halogenated / chemical synthesis*
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Hydrocarbons, Halogenated / chemistry*
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Molecular Structure
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Palladium / chemistry
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Potassium / chemistry*
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Stereoisomerism
Substances
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Acetamides
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Alkenes
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Borates
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Chloroacetates
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Hydrocarbons, Halogenated
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Palladium
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Potassium