516-12-1 N-Iodosuccinimide (NIS)
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Source of positive iodine. Iodinates methoxy benzenes and naphthalenes in acetonitrile, e.g. anisole gives 95% yield of 4-iodoanisole: Tetrahedron Lett., 37, 4081 (1996). In combination with TFA and TFA anhydride, iodinates 2,4-diethoxypyrimidines or N-alkyluracils specifically to their 5-iodo-derivatives: Synth. Commun., 18, 855 (1988). With triflic acid, the "superelectrophile" iodine(I) triflate is formed. This species will iodinate even deactivated aromatics, e.g. nitrobenzene to the m-iodo derivative: J. Org. Chem., 58, 3194 (1993). Alone or with a catalytic amount of triflic acid, is a powerful coupling agent in oligosaccharide synthesis, particularly for thioglycosyl donors; see, e.g.: Tetrahedron Lett., 34, 8523 (1993). For reviews, see: Chem. Rev., 93, 1503 (1993); Contemp. Org. Synth., 3, 173 (1996).
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