Convergent, regiospecific synthesis of quinolines from o-aminophenylboronates.
A direct convergent two-component synthesis of quinolines from alpha,beta-unsaturated ketones and o-aminophenylboronic acid derivatives is reported. The reaction is regiocomplementary to the traditional Skraup-Doebner-Von Miller synthesis and proceeds under basic rather than strongly acidic conditions. Quinolines substituted in the benzenoid ring can be accessed by using substituted o-aminophenylboronates prepared by direct palladium-catalyzed borylation of the corresponding o-bromoanilines.
Horn
Joachim
J
School of Chemistry, University of Leeds, Leeds LS2 9JT, UK.
Marsden
Stephen P
SP
Nelson
Adam
A
House
David
D
Weingarten
Gordon G
GG
D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D010165:Palladium / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
D001897:Boronic Acids; D011804:Quinolines; C028592:3-aminobenzeneboronic acid; D010165:Palladium