Tsuji-Trost Type Functionalization of Allylic Substrates with Challenging Leaving Groups: Recent Developments

Author(s): Raffaella Ferraccioli, Luca Pignataro.

Journal Name: Current Organic Chemistry

Volume 19 , Issue 2 , 2015

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Graphical Abstract:


The Review reports the recent developments of palladium-catalyzed nucleophilic substitution of allylic alcohols and allylic amines used as electrophiles. The poor ability of the hydroxyl and amino groups to serve as good leaving groups has been overcome by the employment of additives which promote the palladium-catalyzed C-N and C-O bond cleavage. However, allylic alcohol and amine activation can be achieved by using appropriate catalytic systems or solvents, without any external activators. Significant expansion of the nucleophile scope allows to obtain various allylic compounds through the regio- and stereoselective formation of carbon-carbon and carbonheteroatom bonds.

Keywords: Additive, allylic alcohol, allylic amine, electrophile, nucleophile, palladium, Tsuji-Trost reaction.

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Article Details

Year: 2015
Page: [106 - 120]
Pages: 15
DOI: 10.2174/1385272819666150122232013
Price: $58

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PDF: 51