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.
2015
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]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11388/47701
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