Arene-catalysed lithiation of 1,4-dichlorobut-2-enes and 3,4-dichlorobut-1-ene and reaction with electrophiles: A common reaction pathway

Add time:08/26/2019    Source:sciencedirect.com

The reaction of (Z) or (E)-1,4-dichlorobut-2-ene (1,2), or 3,4-diclorobut-1-ene (3) with an excess of lithium powder and a catalytic amount of 4,4′-di-tert-butylbiphenyl (5 mol %) in the presence of an electrophile [(CH2)4CO, ButCHO, Me3SiCl] in THF at O°C yields, after hydrolysis, the corresponding 1,4- and 1,2-disubstituted compounds (Z/E)-4 and 5, the ratio of them being independent on the starting material. In the case of compounds 4 the Z-diastereomer is largely the major one. When dichlorodiethylsilane was used as electrophile the corresponding substituted silacyclopentene 6 was the only reaction product isolated. A possible mechanism involving dilithiated species is proposed.

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