Affiliation:
1. Stratingh Institute for Chemistry University of Groningen Nijenborgh 4 9747 AG Groningen The Netherlands
Abstract
Abstractα,β‐Unsaturated ketones are highly versatile intermediates in organic synthesis, widely being used as substrates in e. g. 1,4‐addition‐ and Diels‐Alder reactions. Their synthesis, however, often proceeds via multi‐step pathways. Here we present an alternative methodology for the one‐pot formation of 1‐aryl‐2‐buten‐1‐ones by the Pd‐catalysed cross‐coupling of readily available bromides and lithium 1‐methoxy‐1,3‐butadienes, proceeding in 2.5 h at 40 °C. In situ hydrolysis of the intermediate 1‐aryl‐1‐methoxy‐1,3‐butadienes affords the desired 1‐aryl‐2‐buten‐1‐ones, providing a direct cross‐coupling method to access isomerically pure (E)‐enones.
Funder
Nederlandse Organisatie voor Wetenschappelijk Onderzoek
Koninklijke Nederlandse Akademie van Wetenschappen
Ministry of Education, Culture, Sports, Science and Technology