Dataset Information
Understanding Site Selectivity in the Palladium-Catalyzed Cross-Coupling of Allenylsilanolates.
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ABSTRACT:
SUBMITTER: Denmark SE
PROVIDER: S-EPMC5997285 | biostudies-literature | 2017 Nov
REPOSITORIES: biostudies-literature
Publications
Understanding Site Selectivity in the Palladium-Catalyzed Cross-Coupling of Allenylsilanolates.
Synlett : accounts and rapid communications in synthetic organic chemistry 20170712 18
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 reactiv ...[more]