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41.1.1.5.11.2 Variation 2: Palladium-Catalyzed Allylation

DOI: 10.1055/sos-SD-041-00002

Aitken, R. A.; Aitken, K. M.Science of Synthesis, (201041131.

Adding a palladium catalyst, most commonly tetrakis(triphenylphosphine)palladium(0), to a mixture of a nitroalkyl salt and an allyl halide or equivalent gives good yields of allylated nitroalkanes, where the nitroalkyl group is introduced selectively at the less hindered end of the allyl system. This arises from the reaction mechanism, which proceeds via the palladium π-allyl complex 307 (Scheme 177). 1-Chlorobut-2-ene (306) and 3-chlorobut-1-ene (309) thus give the same product 308 when they are treated with 2-nitropropane in methanol using sodium methoxide as a base and tetrakis(triphenylphosphine)palladium(0) generated in situ from triphenylphosphine and dichlorobis(triphenylphosphine)palladium(II).[‌515‌]

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