Switchable Synthesis Of Indenes And Naphthalenes By Transannulation Of 1-Sulfonyl-4-(2-alkenylphenyl)-1,2,3-Triazoles

1-Sulfonyl-1,2,3-triazole can produce ?-imine rhodium carbene in the presence of transition metal rhodium.Because of the electrophilic carbene carbon atom and the nucleophilic imine nitrogen atom,?-imine rhodium carbene could undergo many important chemical reactions,such as cyclopropanation,X-H insertion,1,2-migration and many other types of carbene-induced reactions.As a result,this important intermediate could be widely used in the synthesis of many N-containing compounds.In addition,a number of cyclic compounds can be synthesized by ketenimine,an important intermediate generated from 1-sulfonyl-1,2,3-triazole under thermal conditions.This thesis mainly focuse on the switchable synthesis of indenes and naphthalenes by transannulation of 1-sulfonyl-4-(2-alkenylphenyl)-1,2,3-triazoles.Indene derivatives were generated by rhodium catalysis and naphthalene derivatives were formed under thermal conditions(1)Rhodium catalyzed cyclization reaction of 1-sulfonyl-4-(2-alkenylphenyl)-1,2,3-triazoles for the synthesis of indene derivatives: The optimized reaction conditions were established: Under a nitrogen atmosphere,3 mol% of Rh2(piv)4 as catalyst,1,2-DCE as solvent at reflux.Most 1-sulfonyl-4-(2-alkenylphenyl)-1,2,3-triazoles in 1,2-DCE investigated reacted smoothly under the standard conditions to afford indene derivatives in moderate to high yields.Several unstable products can be obtained one-pot-two-steps transannulation and reduction of the corresponding 1-sulfonyl-4-(2-alkenylphenyl)-1,2,3-triazoles.(2)Thermally induced denitrogenative annulation of 1-sulfonyl-4-(2-alkenylphenyl)-1,2,3-triazole for the synthesis of naphthalene derivatives: The optimized reation conditions were as follows: under nitrogen atmosphere,1,2-DCE as solvent and at reflux.Naphthalene derivatives could be obtained good yields.Most triazoles investigated could afford the corresponding naphthalene derivatives and many functional groups were well tolerated in the reaction.In addition,few substrates produced both indene and naphthalene products.