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The intramolecular oxidative coupling of electron-rich aromatic groups in 5-(het)aryl-1-(het)arylalkyl-1H-1,2,3-triazoles was studied in detail. Under treatment with phenyliodoso bis(trifluoroacetate) and boron trifluoride etherate these substrates afforded products of either ortho/ortho… Click to show full abstract
The intramolecular oxidative coupling of electron-rich aromatic groups in 5-(het)aryl-1-(het)arylalkyl-1H-1,2,3-triazoles was studied in detail. Under treatment with phenyliodoso bis(trifluoroacetate) and boron trifluoride etherate these substrates afforded products of either ortho/ortho or ortho/ipso coupling depending on the nature of aromatic groups and reaction conditions applied. It was found that for substrates which are capable for both types of coupling, ortho-/ipso-adducts are formed under kinetic control while ortho-/ortho-products are formed under thermodynamic control. The developed procedures allow preparation of complex polycyclic azaheterocycles from simple precursors in two steps only.
Journal Title: Chemistry of Heterocyclic Compounds
Year Published: 2021
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