A ruthenium-catalysed dehy drogenativecross-coupling of primary alcohols and imines inthe presence of TFA provided a library of different-ly substituted quinolines. Imines can be prepared insitu from various anilines and several benzyl alco-hols using a ruthenium-catalysed hydrogen-transferprocedure. Without changing the catalyst, quino-lines can be obtained in moderate to good yields byadding various primary alcohols in the presence ofTFA (30 mol%) via a “telescopic” protocol. Theuse of alcohols, the absence of strong oxidants andthe diversity of potential starting materials makethis modern version of the Skraup reaction superi orto most of the conventional quinoline syntheses.
A mild and efficient synthesis of substituted quinolines via a cross-dehydrogenative coupling of (Bio)available alcohols and aminoarenes / Mura, Manuel Giacomo; Rajamäki, Suvi; DE LUCA, Lidia Vera Giovanna; Cini, Elena; Porcheddu, Andrea. - In: ADVANCED SYNTHESIS & CATALYSIS. - ISSN 1615-4150. - 357:2-3(2015), pp. 576-582. [10.1002/adsc.201400815]
A mild and efficient synthesis of substituted quinolines via a cross-dehydrogenative coupling of (Bio)available alcohols and aminoarenes
MURA, Manuel Giacomo;DE LUCA, Lidia Vera Giovanna;PORCHEDDU, Andrea
2015-01-01
Abstract
A ruthenium-catalysed dehy drogenativecross-coupling of primary alcohols and imines inthe presence of TFA provided a library of different-ly substituted quinolines. Imines can be prepared insitu from various anilines and several benzyl alco-hols using a ruthenium-catalysed hydrogen-transferprocedure. Without changing the catalyst, quino-lines can be obtained in moderate to good yields byadding various primary alcohols in the presence ofTFA (30 mol%) via a “telescopic” protocol. Theuse of alcohols, the absence of strong oxidants andthe diversity of potential starting materials makethis modern version of the Skraup reaction superi orto most of the conventional quinoline syntheses.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.