Unified Approach to (Thio)chromenones via One-Pot Friedel–Crafts Acylation/Cyclization: Distinctive Mechanistic Pathways of β-Chlorovinyl Ketones

DOI: 10.1021/acs.orglett.6b03348

Friedel–Crafts Arylation for the Formation of C sp 2[BOND]C sp 2 Bonds: A Route to Unsymmetrical and Functionalized Polycyclic Aromatic Hydrocarbons from Aryl Triazenes

Superacid-catalyzed Friedel–Crafts cyclization of unactivated alkenes

Practical synthesis of aromatic nitriles via gallium-catalysed electrophilic cyanation of aromatic C–H bonds

Chem. Commun., 2012, 48, 3127-3129

Oxidative Prins and Prins/Friedel–Crafts cyclizations for the stereoselective synthesis of dioxabicycles and hexahydro-1H-benzo[f]isochromenes via the benzylic C–H activation

1-Benzyl ethers of (E)- and (Z)-hex-3-en-1,6-diols and hept-3-en-1,7-diols undergo a smooth oxidative cyclization with DDQ in the presence of In(OTf)₃ through a sequential C–H bond activation and an intramolecular Prins cyclization to afford the corresponding trans- and cis-fused hexahydro-2H-furo[3,2-c]pyrans and octahydropyrano[4,3-b]pyrans respectively in good yields with an excellent stereoselectivity. Aryl tethered homoallylbenzyl ethers such as benzyl ethers of (E)- and (Z)-6-arylhex-3-enyl alcohols undergo a tandem Prins/Friedel–Crafts cyclization in the presence of stoichiometric amounts of DDQ and SnCl₄via the benzylic C–H bond activation to furnish the corresponding trans- and cis-fused hexahydro-1H-benzo[f]isochromenes in good yields with complete stereoselectivity.