Regioselective Reductive Demethoxylation of 3,4,5‐Trimethoxystilbenes.

Azzena, Ugo; Dettori, Giovanna; Idini, Maria Vittoria; Pisano, Luisa; Sechi, Grazia

doi:10.1002/chin.200404077

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“…The reaction, can be rationalized as the result of a competition between reductive demethoxylation [132] and addition of the alkali metal to the carbon -carbon double bond, leading to the intermediate formation of a vic-diorganometal (232); oxidation of the latter with Br(CH 2 ) 2 Br allowed the recovery of the corresponding (E)-stilbene (233), whilst quenching with H 2 O (or D 2 O) led to the formation of the corresponding bibenzyl derivative (234) (Scheme 59) [131].…”

Section: 2-diarylsubstituted Alkenesmentioning

confidence: 99%

“…Besides reacting as dinucleophiles, these vic-diorganometals find employment as versatile reducing agents which, from a practical point of view, can be considered as synthetic equivalents of an activated and highly reactive form of an alkali metal that, however, function under homogeneous and mild reaction conditions. Recent interest in this field originated with the development of a new approach to the synthesis of resorcinolic stilbenes and bibenzyls, an important class of natural products endowed with interesting biological and pharmacological properties [131].…”

Section: 2-diarylsubstituted Alkenesmentioning

confidence: 99%

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Benzylic Organometals via Reductive Metalation Procedures

Azzena¹,

Dettori²,

Pisano

2011

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The review discusses two different reductive metalation approaches to the generation of benzylic organometals.In the first part, the scope of the generation of polar benzylic organometals by the reductive cleavage of carbon -heteroatom sigma bonds will be presented. Besides briefly showing the evolution of the technique, the review deals with recent achievements in the generation of benzylic derivatives of alkali metals by the reductive cleavage of carbon -halogen, carbon -oxygen, carbon -nitrogen and carbon -sulphur bonds. Significant synthetic applications of this procedure are described, showing that an appropriate choice of reaction conditions (solvent, temperature, alkali metal, employment of an electron shuttle) strongly affects the outcome of the cleavage reaction.In the second part, the application of the reductive metalation to carbon -carbon, carbon -oxygen and carbon -nitrogen double bonds is described, a procedure leading to the generation of vic-diorganometallic derivatives. Synthetic applications of these diorganometals are illustrated, underlining the possible application of 1,2-diarylsubstituted vic-dicarbanions as synthetic analogues of an activated form of an alkali metal that, however, function under homogeneous and mild reaction conditions.

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Section: 2-diarylsubstituted Alkenesmentioning

confidence: 99%

Section: 2-diarylsubstituted Alkenesmentioning

confidence: 99%