Synthesis of Acrylamides via the Doebner–Knoevenagel Condensation

A selective synthesis of acrylamides had been developed using the Doebner–Knoevenagel condensation. The reaction occurs under mild conditions at ambient temperatures, tolerates a wide array of functional groups, and affords the E-isomer with high selectivity. The reported method expands the scope of...

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Veröffentlicht in:Journal of organic chemistry 2019-05, Vol.84 (10), p.6465-6474
1. Verfasser: Zacuto, Michael J
Format: Artikel
Sprache:eng
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Zusammenfassung:A selective synthesis of acrylamides had been developed using the Doebner–Knoevenagel condensation. The reaction occurs under mild conditions at ambient temperatures, tolerates a wide array of functional groups, and affords the E-isomer with high selectivity. The reported method expands the scope of this classic reaction to a class of industrially important products and as well as to the use of aliphatic aldehydes. An organocatalytic mechanism has been proposed, and the ability to scale the process has been demonstrated.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b00450