Palladium-Catalysed Coupling Reactions: (Z)-Vinyl (N,N-Diisopropyl)carbamate Group as an Efficient Precursor of a (Z)-Vinyl Triflate Function

Abstract

A (Z)-vinyl (diisopropyl)carbamate group, generated from a Hoppe allylation reaction, was easily transformed either into the corresponding (Z)-vinyl phosphate or (Z)-vinyl triflate function in good yield and high selectivity. It was also shown that the resulting (Z)-vinyl triflate compound could be utilized successfully in palladium-catalysed coupling reactions with vinyl-, phenyl- and acetylenic tin derivatives, without loss of the (Z)-geometry of the double bond.

Key words

palladium - alkenes - coupling - allylations - tin

References

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23

A (Z)-vinyl carbamate could be also easily obtained by treatment of an allyl carbamate under the following condiditons:^5d BuLi, TMEDA, Ti(OPr-i)₄, -78 °C, H₃O⁺.