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Ruthenium Catalysts for Controlled Mono‐ and Bis‐Allylation of Active Methylene Compounds with Aliphatic Allylic Substrates
Author(s) -
Zhang HuiJun,
Demerseman Bernard,
Xi Zhenfeng,
Bruneau Christian
Publication year - 2009
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200900498
Subject(s) - ruthenium , chemistry , allylic rearrangement , malononitrile , catalysis , methylene , combinatorial chemistry , medicinal chemistry , organic chemistry
The allylation of 1,3‐dicarbonyl compounds and malononitrile with aliphatic allylic substrates is achieved under mild conditions in the presence of new ruthenium catalysts. The ruthenium complex [Ru(C 5 Me 5 )(2‐quinolinecarboxylato)(CH 2 CHCH‐ n ‐Pr)] [BF 4 ] as a precatalyst, allows the synthesis of mono‐allylated branched derivatives. On the other hand, the parent complex [Ru(C 5 Me 5 )(MeCN) 3 ] [PF 6 ] as a precatalyst, straightforwardly favours the bis‐allylation of the procarbonucleophiles leading to bis‐allylated bis‐linear products. The involvement of the two precatalysts provides a sequential synthesis of unsymmetrical mixed linear‐branched bis‐allylated derivatives.