Organophosphine-Catalyzed Intramolecular Hydroacylation of Activated Alkynes

Organophosphine-Catalyzed Intramolecular Hydroacylation of Activated Alkynes

We present the details of an organophosphine-catalyzed Morita–Baylis–Hillman-type reaction of activated alkynes. The outcome is an intramolecular hydroacylation of α,β-ynones leading to the formation of 1,3-cyclopenta-, cyclohepta-, and cyclooctadione-fused arenes and heteroarenes. In addition, duri...

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Veröffentlicht in:ACS catalysis 2018-04, Vol.8 (4), p.2748-2753
Hauptverfasser: Mondal, Atanu, Hazra, Raju, Grover, Jagdeep, Raghu, Moluguri, Ramasastry, S. S. V
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creator Mondal, Atanu
Hazra, Raju
Grover, Jagdeep
Raghu, Moluguri
Ramasastry, S. S. V
description We present the details of an organophosphine-catalyzed Morita–Baylis–Hillman-type reaction of activated alkynes. The outcome is an intramolecular hydroacylation of α,β-ynones leading to the formation of 1,3-cyclopenta-, cyclohepta-, and cyclooctadione-fused arenes and heteroarenes. In addition, during the course of the investigation, a phosphine-catalyzed intramolecular aldol reaction of keto-ynones via δ′[C­(sp3)-H]-functionalization was discovered, and a new annulation event comprising of a ω′[C­(sp3)-H]-functionalization of α,β-ynones was also uncovered. The mechanisms governing these processes have been thoroughly elucidated.
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