Access to CF-benzofulvenes palladium-catalyzed cascade arylation/Trost-Oppolzer cyclization/double-bond isomerization

Herein, we demonstrated a Pd-catalyzed cascade reaction that involves arylation, Trost-Oppolzer type Alder ene reaction, and double bond isomerization using the 4-(2-alkynylphenyl)-allylcarbonates and aryl boronic acids. This cascade process delivers a wide array of distinctive functionalized CF 3 -...

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Published in:Chemical communications (Cambridge, England) England), 2024-03, Vol.6 (26), p.3551-3554
Main Authors: Sateesh, Rami, Prudhviraj, Jaggaraju, Priyanka, Chiliveru, Punna, Nagender
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Summary:Herein, we demonstrated a Pd-catalyzed cascade reaction that involves arylation, Trost-Oppolzer type Alder ene reaction, and double bond isomerization using the 4-(2-alkynylphenyl)-allylcarbonates and aryl boronic acids. This cascade process delivers a wide array of distinctive functionalized CF 3 -benzofulvenes in good yields with high stereoselectivity ( E ). A single palladium catalyst orchestrates the two individual reactions in a single operation. Trost-Oppolzer type Alder ene reaction is the key in this transformation, also called a rare acid-free iso-Nazarov type cyclization. Highly stereoselective synthesis of CF 3 -benzofulvenes has been achieved through a Pd-catalyzed cascade reaction involving three consecutive transformations such as arylation, Trost-Oppolzer type Alder-ene reaction, and double bond isomerization.
ISSN:1359-7345
1364-548X
DOI:10.1039/d3cc06082a