ArticleSynlett : accounts and rapid communications in synthetic organic chemistry2017
Understanding Site Selectivity in the Palladium-Catalyzed Cross-Coupling of Allenylsilanolates.
Article in Synlett : accounts and rapid communications in synthetic organic chemistry, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Abstract
Allenylsilanolates can undergo cross-coupling at the α- or γ-terminus, and site selectivity appears to be determined by the intrinsic transmetalation mechanism. Fine-tuning of concentration, nucleophilicity, and steric bulk of the silanolate moiety allows for the selective formation of one isomer over the other. Whereas the α-isomer can be obtained in synthetically useful yield, the γ-isomer is favored only when employing reaction conditions that are inevitably associated with diminished reactivity.
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