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Reaction of arynes with trifluoroacetylated β‐diketones: Novel formation of isocoumarins and phenanthrenes

Reaction of arynes with trifluoroacetylated β‐diketones: Novel formation of isocoumarins and... Polysubstituted isocoumarins were synthesized by the reaction of substituted 2‐(trimethylsilyl)aryl triflates with trifluoromethylated β‐diketones in the presence of CsF. The reaction proceeded through carbon‐carbon bond insertion of aryne and intramolecular cyclization to form intermediates of alcohol anions, which extruded trifluoromethyl anion to afford isocoumarins. By using CuBr as a catalyst, 2 eq. of aryne reacted with β‐diketones to afford phenanthrenes and 1,2‐diarylethanones. Although reaction of 2‐(trimethylsilyl)phenyl triflate with 1,1,1‐trifluoro‐4′‐methylbenzoylacetone in the presence of CsF gave 3‐(4′‐methylphenyl)isocoumarin in 67% yield, addition of 0.2 eq. of CuCN resulted in the formation of 9‐(4‐methylbenzoyl)‐10‐trifluoromethylphenanthrene in 35% yield. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Heteroatom Chemistry Wiley

Reaction of arynes with trifluoroacetylated β‐diketones: Novel formation of isocoumarins and phenanthrenes

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References (47)

Publisher
Wiley
Copyright
"Copyright © 2018 Wiley Periodicals, Inc."
ISSN
1042-7163
eISSN
1098-1071
DOI
10.1002/hc.21444
Publisher site
See Article on Publisher Site

Abstract

Polysubstituted isocoumarins were synthesized by the reaction of substituted 2‐(trimethylsilyl)aryl triflates with trifluoromethylated β‐diketones in the presence of CsF. The reaction proceeded through carbon‐carbon bond insertion of aryne and intramolecular cyclization to form intermediates of alcohol anions, which extruded trifluoromethyl anion to afford isocoumarins. By using CuBr as a catalyst, 2 eq. of aryne reacted with β‐diketones to afford phenanthrenes and 1,2‐diarylethanones. Although reaction of 2‐(trimethylsilyl)phenyl triflate with 1,1,1‐trifluoro‐4′‐methylbenzoylacetone in the presence of CsF gave 3‐(4′‐methylphenyl)isocoumarin in 67% yield, addition of 0.2 eq. of CuCN resulted in the formation of 9‐(4‐methylbenzoyl)‐10‐trifluoromethylphenanthrene in 35% yield.

Journal

Heteroatom ChemistryWiley

Published: Dec 1, 2018

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