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C−H Bond Functionalization via Hydride Transfer: Direct Coupling of Unactivated Alkynes and sp 3 C−H Bonds Catalyzed by Platinum Tetraiodide

2009; American Chemical Society; Volume: 131; Issue: 45 Linguagem: Inglês

10.1021/ja906480w

1943-2984

Paul A. Vadola, Dalibor Sameš,

Cyclopropane Reaction Mechanisms

We report a catalytic intramolecular coupling between terminal unactivated alkynes and sp3 C−H bonds via through-space hydride transfer (HT-cyclization of alkynes). This method enables one-step preparation of complex heterocyclic compounds by α-alkenylation of readily available cyclic ethers and amines. We show that PtI4 is an effective Lewis acid catalyst for the activation of terminal alkynes for hydride attack and subsequent C−C bond formation. In addition, we have shown that the activity of neutral platinum salts (PtXn) can be modulated by the halide ligands. This modulation in turn allows for fine-tuning of the platinum center reactivity to match the reactivity and stability of selected substrates and products.