Remarkable Switch in the Regiochemistry
of the Iodination of Anilines by N-Iodosuccinimide:
Synthesis of 1,2-Dichloro-3,4-diiodobenzene

Hao Shen; K. Peter C. Vollhardt

doi:10.1055/s-0031-1290118

LETTER

Remarkable Switch in the Regiochemistry of the Iodination of Anilines by N-Iodosuccinimide: Synthesis of 1,2-Dichloro-3,4-diiodobenzene

Hao Shen, K. Peter C. Vollhardt*
Department of Chemistry, University of California at Berkeley, Berkeley, CA 94720-1460, USA
Fax: +1(510)6435208; e-Mail: kpcv@berkeley.edu;

Abstract

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Abstract

Direct iodination of anilines by NIS in polar solvents (such as DMSO) affords p-iodinated products with up to >99% regioselectivity. Switching to less polar solvents (such as benzene) in the presence of AcOH inverts this outcome toward dramatically increased or preferential generation of the o-isomers, also with up to >99% regioselectivity. This finding was exploited in the synthesis of 1,2-dichloro-3,4-diiodobenzene.

Key words

aromatic amine - electrophilic substitution - halogenation - regioselectivity - solvent effects

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Referenzen

References and Notes

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