[1,2]- or [2,3]-rearrangement of onium ylides of allyl and benzyl ethers and sulfides via in situ-generated iodonium ylides.
Iodonium ylides, generated in situ with bisacetoxyiodobenzene, are converted to allyl- or benzyl-substituted oxonium or sulfonium ylides via rhodium- or copper-catalyzed carbene transfer. Except for the S-benzyl example, the resulting ylides undergo rearrangement to the corresponding 2-substituted heterocycles. This demonstrates the first use of iodonium ylides as diazoketone surrogates for the generation and rearrangement of onium ylide intermediates. This abbreviated one-step method proceeds in comparable yields relative to the corresponding two-step route employing diazoketone intermediates.
Murphy
Graham K
GK
Department of Chemistry, University of Alberta, Edmonton, AB, Canada T6G 2G2.
West
F G
FG
D004987:Ethers / Q000737:chemistry*; D007455:Iodine / Q000737:chemistry*; D013440:Sulfides / Q000737:chemistry*
D004987:Ethers; D013440:Sulfides; D007455:Iodine