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Tin-free radical reactions have attracted a great deal of attention in recent years. 1 To obviate the problem of using highly toxic organotin compounds, several approaches have been developed and include fluorous 2 or polymer-supported organotins, 3 organosilyl substitutes, 4 and thiocarbonyl and organosulfone derivatives. 5 The organosulfone-mediated approach is very effective for allylation, 6 vinylation, and azidation. 8 However, the reported methods did not work well with primary alkyl iodides and xanthates due to inefficient iodine atom and xanthate group transfers, respectively. We reported a highly efficient indirect approach for a radical acylation using phenylsulfonyl oxime ether under tinmediated conditions (eq. 1) 9 and also developed tin-free acylation approach using methanesulfonyl oxime ether, in which primary alkyl iodides and xanthates caused the same problem due to a small energy difference between a methyl radical and a primary alkyl radical (eq. 2). 10

Tin-free Radical Acylation Reactions Using Alkyl Allyl Sulfones as Radical Precursors