Science of Synthesis

Marsden, S. P., Science of Synthesis, (2005) 26, 1062.

Alkenoylpalladium(II) species can also be generated by carbonylation of alkenylpalladi­um(II) reagents and their coupling reactions with organometallic reagents constitute a viable route to enones. The alkenoylpalladium(II) species can be prepared from alkenyl halides or trifluoromethanesulfonates, e.g. ‌78‌ and ‌80‌ (‌Scheme 19‌). Boranes are competent nucleophiles for the coupling reaction and 9-alkyl-9-borabicyclo[3.3.1]nonanes are particularly useful reagents, since only the desired alkyl chain is transferred in the reaction to give products ‌79‌.[‌73‌] Alternatively, borate salts such as ‌81‌, prepared by the addition of organolithiums to trialkylboranes, are also selective group-transfer reagents.[‌74‌] Organ­ostannanes can be employed as coupling partners, as in the synthesis of the crossed enynone ‌83‌ from alkynylstannane ‌82‌.[‌75‌]

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References

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• 8.Meeeee-Meee, (8888) M 88-8, 888.
• 8.Meeeee-Meee, (8888) M 88-8, 888.