The photochemistry of noncovalent interactions to promote organic transformations is an emerging approach to providing fresh opportunities in synthetic chemistry. Generally, the external substance is necessary to add as an interaction partner, thereby sacrificing the atom economy of the reaction. Herein, we describe a catalyst-free and noncovalent interaction-mediated strategy to access the olefination of N-tosylhydrazones using acetone as a solvent and an interaction partner. This protocol also features broad substrate scope, excellent functional group compatibility, and mild reaction conditions without transition metals. Moreover, the gram-scale synthesis of olefins and the generation of pharmaceutical intermediates highlighted its practical applicability. Lastly, mechanistic studies indicate that the reaction was initiated via noncovalent interactions between acetone and N-tosylhydrazone anion, which is also supported by density functional theory calculations.

中文翻译：

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丙酮作为溶剂和相互作用伙伴促进可见光下 N-甲苯磺酰腙的直接烯化

促进有机转化的非共价相互作用的光化学是一种新兴方法，为合成化学提供了新的机会。通常，需要添加外部物质作为相互作用伙伴，从而牺牲了反应的原子经济性。在此，我们描述了一种无催化剂和非共价相互作用介导的策略，使用丙酮作为溶剂和相互作用伙伴来实现N-甲苯磺酰腙的烯化。该方案还具有广泛的底物范围、优异的官能团兼容性以及不含过渡金属的温和反应条件等特点。此外，克级烯烃的合成和医药中间体的生成凸显了其实际应用性。最后，机理研究表明该反应是通过丙酮和N-甲苯磺酰腙阴离子之间的非共价相互作用引发的，这也得到了密度泛函理论计算的支持。