α-Vinyl-carbonyl compounds are a class of orthogonally functionalized molecules, wherein the intrinsic C═O and C═C bonds can be used to unlock distinctly different reactivities. In this report, we present a simple method for the direct α-vinylation of carbonyl compounds utilizing vinyltriarylbismuthonium (“Vinyl-Bis”) salts, which are stable and readily preparable on a decagram scale. This transformation is accomplished efficiently through the reaction of an in situ generated Li-enolate intermediate with a Vinyl-Bis reagent, leading to the formation of α-vinylated carbonyl compounds in good to excellent yields and with a remarkably broad substrate scope. Critically, this vinylation method is effective for enolates generated via numerous methods, enabling the sequencing of reactions that generate enolates with the vinylation step and the ready synthesis of diversely functionalized compounds, thereby underscoring the versatility and practicality of this method. Analogous reactions of discrete Li-enolates with other vinyl units and with aryl groups are also demonstrated.

中文翻译：

---

乙烯基三芳基铋盐：羰基化合物 α-乙烯基化的强大载体


α-乙烯基-羰基化合物是一类正交官能化分子，其中固有的 C=O 和 C=C 键可用于解锁明显不同的反应性。在本报告中，我们提出了一种利用乙烯基三芳基铋鎓（“乙烯基-Bis”）盐直接对羰基化合物进行α-乙烯基化的简单方法，该盐稳定且易于在十克规模上制备。这种转化是通过原位生成的烯醇锂中间体与乙烯基双试剂的反应有效完成的，从而以良好至优异的产率和非常广泛的底物范围形成α-乙烯基化羰基化合物。至关重要的是，这种乙烯基化方法对于通过多种方法生成的烯醇化物是有效的，能够对通过乙烯基化步骤生成烯醇化物的反应进行排序，并易于合成不同官能化的化合物，从而强调了该方法的多功能性和实用性。还证明了离散的烯醇化物与其他乙烯基单元和芳基的类似反应。