CO(2) Unlocks Reactivity: Boryl Silyl Ketene Acetals Enable Mild and Direct C═C Bond Cleavage

CO(2) 释放反应活性:硼基硅基烯酮缩醛可实现温和直接的 C═C 键断裂

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Abstract

Boron-ligand cooperation (BLC) has emerged as a powerful principle of bond activation with main-group elements, yet pyridine-based systems have so far eluded experimental evidence of CO(2) activation. We show here that four-membered pyridyl-boracycles activate CO(2) through a dearomatizing boron-carbon bond cleavage, unambiguously proceeding by a BLC rather than a B/N-FLP-type mechanism, as confirmed by density functional theory (DFT) studies, in contrast to previously predicted computational pathways. This process furnishes boryl silyl ketene acetals, a hitherto unknown class of enolate equivalents in which the two oxygen atoms are differentiated by boryl and silyl substituents. These intermediates exhibit remarkable follow-up reactivity, eventually leading to a mild, one-step C═C double-bond cleavage that delivers fulvene derivatives under additive-free conditions, thereby constituting an unprecedented form of metathesis. Overall, our findings establish boryl silyl ketene acetals derived from CO(2) as a novel class of main-group systems that unlock a reactivity platform with far-reaching synthetic implications.

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