GENERATION OF MONOARYL-λ~3-IODANES FROM ARYLBORON COMPOUNDS THROUGH IPSO-SUBSTITUTION

摘要

Monoaryl-λ~3-iodanes serve as versatile oxidants and arylating reagents in organic synthesis.In addition to the oxidation of iodoarenes,electrophilic aromatic substitution reactions using iodine tricarboxylates have been used for the synthesis of monoaryl-λ~3-iodanes.Here,we report that ipso-substitution reactions of aryltrifluoroborates with iodine tris(trifluoroacetate)in DMF or DMA smoothly produced monoaryl-λ~3-iodanes,which were readily converted to aryliodonium ylides.We also demonstrated that sequential C-H borylation and the ipso-substitution efficiently introduced the I(III)group under steric control.