Heterocycles by PtCl2-Catalyzed Intramolecular Carboalkoxylation or 
Carboamination of Alkynes

Fürstner, Alois; Davies, Paul W.

doi:10.1021/ja055659p

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Heterocycles by PtCl₂-Catalyzed Intramolecular Carboalkoxylation or Carboamination of Alkynes

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Fürstner, Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Davies, Paul W.
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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引用

Fürstner, A., & Davies, P. W. (2005). Heterocycles by PtCl₂-Catalyzed Intramolecular Carboalkoxylation or Carboamination of Alkynes. Journal of the American Chemical Society, 127(43), 15024-15025. doi:10.1021/ja055659p.

引用: https://hdl.handle.net/11858/00-001M-0000-0025-AA58-5

要旨

PtCl₂ constitutes a convenient catalyst for intramolecular hydroalkoxylation, carboalkoxylation, hydroamination, and carboamination reactions of alkynes, effecting the formation of substituted benzo[b]furan, indole-, and isochromene-1-one derivatives, respectively. This procedure allows for the transfer of (substituted) allyl, methoxymethyl (MOM), benzyloxymethyl (BOM), and (trimethylsilyl)ethoxymethyl (SEM) groups from oxygen to carbon and is compatible with functional groups that are susceptible to oxidative insertion of low valent metal species previously used for similar purposes. Although some of the reactions can even be carried out in air, the rates are significantly increased when conducted under an atmosphere of CO. A mechanistic rationale is proposed, implying activation of the alkyne by the carbophilic Pt(2+) template as the primary step of the catalytic cycle.