Hydroboration and Suzuki–Miyaura Coupling Reactions with the Electronically Modulated Variant of an Ynamine: The Synthesis of ( E)-β-Arylenamides

The first hydroboration of an 1-alkynylamide—the electronically modulated variant of an ynamine—is described. This hydroboration in combination with a Suzuki–Miyaura cross-coupling reaction with aryl bromides or aryl iodides allows a flexible synthesis of ( E)-β-arylenamides and 3-(2′-amidovinyl)ind...

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Bibliographic Details
Published inTetrahedron Vol. 56; no. 43; pp. 8473 - 8480
Main Authors Witulski, Bernhard, Buschmann, Nicole, Bergsträßer, Uwe
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 20.10.2000
Elsevier
Subjects
1-alkynylamides
catalysis
Chemistry
Chemistry, Organic
cross-coupling reaction
hydroboration
palladium
Physical Sciences
Science & Technology
ynamines
catalysis
palladium
cross-coupling reaction
hydroboration
ynamines
1-alkynylamides
CONVENIENT SYNTHESIS
DIELS-ALDER REACTIONS
ONE-POT SYNTHESIS
ACIDS
N-FUNCTIONALIZED 1-ALKYNYLAMIDES
VINYLIC ORGANOBORANES
STEREOSPECIFIC SYNTHESIS
RECEPTOR KINASE INHIBITOR
ESTERS
DERIVATIVES
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Summary:The first hydroboration of an 1-alkynylamide—the electronically modulated variant of an ynamine—is described. This hydroboration in combination with a Suzuki–Miyaura cross-coupling reaction with aryl bromides or aryl iodides allows a flexible synthesis of ( E)-β-arylenamides and 3-(2′-amidovinyl)indoles with high degree of molecular diversity.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(00)00773-0