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35.3.1.3.8.4 Using 1,3-Diiodo-5,5-dimethylhydantoin

DOI: 10.1055/sos-SD-135-00110

Saleh, B. A.; Elliott, M. C.Science of Synthesis Knowledge Updates, (20152402.

During the period of coverage of this review, 1,3-diiodo-5,5-dimethylhydantoin (DIH, 16) has been reported as a new reagent for decarboxylation/iodination to give iodides 17. This reagent acts as initiator and iodine source in a simple metal-free procedure. The original report[‌9‌] includes 23 examples including primary, secondary, and tertiary alkyl carboxylic acids, as well as arenecarboxylic acids. The procedure is tolerant of a range of functionalities, as shown in Scheme 7. Aliphatic carboxylic acids work well. With the secondary carboxylic acid 15 (R1 = trans-2-phenylcyclopropyl), 7% of the cis-iodo(phenyl)cyclopropane is obtained in addition to the trans product. With the benzylic carboxylic acid 15 (R1 =3-O2NC6H4CH2), only 0.5 equivalents of 16 is needed, indicating that both iodine atoms can be efficiently incorporated into the product. However, higher yields are generally obtained when an excess of the reagent is used. Aromatic carboxylic acids work well in this reaction, including those containing additional halogens (e.g., R1 = 2-IC6H4, 2-BrC6H4, 3-IC6H4), although in some cases lower yields are reported (e.g., R1 = 3-IC6H4).

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