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The dichotomy between benzene and fulvene formation in palladium-catalyzed domino tricyclizations of 2-bromotetradec-1-ene-7,13-diynes
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posted on 2023-06-07, 21:16 authored by Stefan Schweizer, Michael Schelper, Claudia Thies, Philip J Parsons, Mathias Noltemeyer, Armin de Meijere2-Bromotetradec-1-ene-7,13-diynes 1, 5, 12 with different substituents at the acetylenic terminus under palladium catalysis have been found to either yield an angularly bisannelated benzene derivative 3 (79%), or fulvene derivatives of type 5 (52-74%) as well as monoannelated fulvenes 13b-e (32-48%). The mechanisms for all three reaction modes most probably involve intramolecular 5-exo-trig carbopalladations of an intermediate 1,3,5-hexatrienyl-6-palladium bromide intermediate.
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- Published
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SynlettISSN
09365214Issue
SP ISSVolume
-Page range
920-922Department affiliated with
- Chemistry Publications
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- No
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- Yes
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2012-02-06Usage metrics
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