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Direct aromatization of chlorohydroazulenones with triflic anhydride: access to chloroazulenyl triflates

✍ Scribed by Sébastien Carret; Jean-Pierre Deprés

Book ID
104095629
Publisher
Elsevier Science
Year
2008
Tongue
French
Weight
216 KB
Volume
49
Category
Article
ISSN
0040-4039

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✦ Synopsis

A direct and efficient aromatization of chlorohydroazulenones has been achieved by using triflic anhydride and then lutidine or tropylium cation to afford selectively chloroazulenes and chloroazulenyl triflates, respectively.

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1-Trialkylsilyl-1-alkynes can be directly coupled with vinyl triflates in the presence of TBAF, 3H 2 O and a catalytic amount of AgI and Pd(PPh 3 ) 4 . Functionalized enynes can thus be obtained in good to excellent yields without prior deprotection of the alkyne.