Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 131, Issue 45, Pages 16525-16528Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja906480w
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Funding
- National Institute of General Medical Sciences [GM060326]
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We report a catalytic intramolecular coupling between terminal unactivated alkynes and sp(3) C-H bonds via through-space hydride transfer (HT-cyclization of alkynes). This method enables one-step preparation of complex heterocyclic compounds by alpha-alkenylation of readily available cyclic ethers and amines. We show that Ptl(4) 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.
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