Sequential O-H/C-H bond insertion of phenols initiated by the gold(I)-catalyzed cyclization of 1-bromo-1,5-enynes.

doi:10.1021/acs.orglett.5b00738

Paper

Sequential O-H/C-H bond insertion of phenols initiated by the gold(I)-catalyzed cyclization of 1-bromo-1,5-enynes.

Published Mar 31, 2015 · Klaus Speck, K. Karaghiosoff, T. Magauer

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Abstract

The development of a sequential O-H/C-H bond functionalization of phenols initiated by the cationic gold(I)-catalyzed cyclization of 1-bromo-1,5-enynes to produce (2-bromocyclopent-2-en-1-yl)phenols is reported. This unprecedented domino transformation efficiently proceeds under mild conditions (5 mol % of (t-Bu)3PAuNTf2, CH2Cl2, 0-23 °C) via an intermediate aryl alkyl ether which collapses at ambient temperature to undergo a 1,2-hydride shift followed by C-H insertion of the phenol.

Study Snapshot

Gold(I)-catalyzed cyclization of 1-bromo-1,5-enynes efficiently produces (2-bromocyclopent-2-en-1-yl)phenols under mild conditions, enabling efficient functionalization of phenols.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Paper

Sequential O-H/C-H bond insertion of phenols initiated by the gold(I)-catalyzed cyclization of 1-bromo-1,5-enynes.

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Citations

Tosylhydrazide-Induced 1,6-Enyne Radical Cyclization under Copper Catalysis: Access to 3,4-Dihydronaphthalen-1(2H)-one Derivatives.

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