Department of Chemistry , Indian Institute of Technology Madras , Chennai 600036 , Tamil Nadu , India.
Org Lett. 2019 Jul 19;21(14):5655-5659. doi: 10.1021/acs.orglett.9b01995. Epub 2019 Jul 8.
An efficient Rh(III)-catalyzed redox-neutral weak -coordinating vinylation and allylation of arylacetamides with allylic acetates are described. A wide variety of arylacetamides containing primary, secondary, and tertiary amides and substituted allylic acetates was compatible for the reaction. The synthesized -vinylated arylacetamides were converted into -vinylated phenyl acetic acid and biologically useful 3-isochromanones. A possible reaction mechanism involving π-allyl rhodium intermediate was suggested and further confirmed through deuterium labeling studies.
本文描述了一种高效的 Rh(III)催化的氧化还原中性弱配位的芳基乙酰胺与烯丙基乙酸酯的乙烯基化和烯丙基化反应。各种含有伯酰胺、仲酰胺和叔酰胺的芳基乙酰胺以及取代的烯丙基乙酸酯都适用于该反应。合成的 -乙烯基化芳基乙酰胺可转化为 -乙烯基化苯乙酸和具有生物应用价值的 3-异苯并呋喃酮。提出了一种可能的反应机理，涉及 π-烯丙基铑中间体，并通过氘标记研究进一步证实。
