Relay Catalysis by Palladium and Brønsted Acid Enables Selective Activation of Cyclopropane for One‐Pot Synthesis of Dihydronaphthofurans From Naphthol Derivatives
Experimental study demonstrates one-pot dihydronaphthofuran synthesis from naphthols via palladium and acid relay catalysis, highlighting an efficient route to fused furans.
Key Points
To develop a selective, one-pot catalytic strategy for synthesizing functionalized dihydronaphthofuran scaffolds directly from naphthols and vinylcyclopropanes.
Designed a dual-catalytic system coupling palladium(0) and a Brønsted acid in a sequential one-pot operation.
Reacted naphthalen-1-ols, naphthalen-2-ols, or naphthalenediols with vinylcyclopropane dicarboxylates via tandem allylic alkylation and intramolecular hydroalkoxylation.
Achieved selective assembly of 1,2-dihydronaphtho[2,1-b]furans and 2,3-dihydronaphtho[1,2-b]furans in 43% to 76% yields.
Demonstrated broad substrate scope and functional group tolerance across naphthols bearing electron-donating groups, electron-withdrawing groups, and diol substitutions.