Science of Synthesis

Gandon, V.; Thorimbert, S.; Malacria, M., Science of Synthesis, (2009) 46, 173.

Nickel-catalyzed three-component coupling between an aldehyde, an organozinc reagent, and an alkyne is a useful method to form an allylic alcohol in a few operational steps.[‌19‌] When applied to trimethyl(prop-2-ynyl)silane, for example, this strategy affords δ-hydrox­ylated allylsilanes ‌1‌ that directly eliminate trimethylsilanol to produce 1,3-dienes ‌2‌ in moderate to good yields (‌Scheme 1‌).[‌17‌] It is noteworthy that diynes may also participate in related nickel-catalyzed reactions to afford 1,3,5-trienes (see Section ‌46.5.1.3.2‌).[‌20‌]

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[(8M)-8-Meeeeeeeeeeee-8-eeee]eeeeeee (‌8‌, M8 = Me; M8 = Me); Meeeeee Meeeeeeee:[‌88‌]

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References