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Gold-Catalyzed C(sp2)?C(sp) Coupling by Alkynylation through Oxidative Addition of Bromoalkynes |
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| Authors: | M?Sc Yangyang Yang M?Sc Jasmin Schießl B?Sc Sirine Zallouz M?Sc Verena Göker Dr Jürgen Gross Dr Matthias Rudolph Dr Frank Rominger Prof?Dr A Stephen K Hashmi |
| Institution: | Organisch-Chemisches Institut, Heidelberg University, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany |
| Abstract: | A gold(I)-catalyzed cascade cyclization–alkynylation of allenoates using alkynyl bromide to generate β-alkynyl-γ-butenolides was investigated. Whereas alkynyl iodides afforded significant amounts of the homo-coupling of two lactone units, alkynyl bromides led to a selective reaction, and a broad functional group tolerance was observed. Under the optimized reaction conditions, it was possible to directly synthesize a large range of β-alkynyl-γ-butenolides in moderate to good yields without the need for any external oxidant. |
| Keywords: | allenes cross-coupling gold catalysis heterocycles oxidative addition |