4.8 Review

Carbocyclisation of alkynes with external nucleophiles catalysed by gold, platinum and other electrophilic metals

Journal

CHEMICAL SOCIETY REVIEWS
Volume 38, Issue 8, Pages 2269-2281

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/b807499m

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This tutorial review covers recent developments in catalytic carbocyclisation of functionalised alkynes with external nucleophiles catalysed by gold, platinum and other electrophilic metals. Substrates of such reactions require a tethered functionality to react with the alkyne to complete a carbocyclic ring. We classify the reactions according to the tethered functionalities to illustrate the diversity of the carbocyclisations; these substrates include: (1) alkyne-alkyne, (2) alkyne-allene, (3) alkyne-alkene, (4) oxo-alkynes and (5) oxo-diynes and triynes. Besides their mechanistic interest, these reactions meet atom economy criteria because complex and functionalised carbocyclic products are easily assembled in a cascade sequence from readily available alkynes and nucleophiles.

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