Hypervalent iodine (HVI) reagents are employed in many different reaction types in organic chemistry. Despite the utility of such reagents, the application of HVI reagents, especially phenyliodonium diacetate (PIDA), has been limited due to its perceived poor solubility in a variety of solvents. To address and investigate these limitations, we synthesized HVI reagents where the substituent of the carboxyl group were longer alkyl chains, specifically an <i>n</i>-propyl and <i>n</i>-nonyl group. The solubility of these reagents, as well as the commonly used PIDA and phenyliodonium bis(trifluoroacetate) (PIFA), were measured in dichloromethane, acetonitrile, diethyl ether, tetrahydrofuran, toluene, and hexanes. The HVI reagents derived from the less polar decanoic acid were more soluble in hexanes and less soluble in acetonitrile than the other reagents. Such differing solubility will allow reactions involving HVI reagents to occur in a wider variety of solvents, empowering chemists to be able to better optimize the solvent in such reactions. Additionally, the measured solubilities of PIDA and PIFA will be useful to the synthetic chemistry community.

Study of the solubility of hypervalent iodine reagents and synthesis of hypervalent iodine reagents with differing solubility

ACS Spring Meeting 2021

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