TETRAHEDRON LETTERS
Pergamon

Tetrahedron Letters 42 (2001) 2089–2092

Aromatic iodination in aqueous solution. A new lease of life for aqueous potassium dichloroiodate
Simon J. Garden,* Jose C. Torres, Simone C. de Souza Melo, Alexandre S. Lima, Angelo C. Pinto ´ and Edson L. S. Lima*
Instituto de Quımica, Departamento de Quımica Organica, Universidade Federal do Rio de Janeiro, Ilha do Fundao, ´ ´ ˆ ˜ Rio de Janeiro, CEP 21945 -970, Brazil
Received 27 November 2000; revised 11 January 2001; accepted 15 January 2001

Abstract—A re-investigation of the use of aqueous potassium dichloroiodate (KICl2) as an iodinating agent for aromatic compounds has found the reagent to be more generally applicable than previously known. The …ver más…

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S. J. Garden et al. / Tetrahedron Letters 42 (2001) 2089–2092

Table 1. Substrates and their respective iodinated products as well as a comparison with literature dataa
Table entry 1 Substrate Methodb; reaction time A; 1 hour Product Yield (%); mp (°C); (recryst.) lit. (%); mp (°C)Ref. 94–97; 190–200sub.; (see Ref. 9); lit. (84–93)c; 198–2009

2

A; 1 hour

80–87; 180–181; (EtOH/H2O); lit. (63–90)d 181–18220

3

C; 6 hours

91; 189–191; (MeOH); lit. (55–80)d 191–1928b

4

A; 6 hours

89; 200 dec.; (MeOH); ----

5

A; 6 hours

79; 200; (MeOH); lit. (64)d 194–1958f

6

A; 6 hours

95; 108–110; (CHCl3); lit. (80)e 108–1103a; (51)c,

7d

7

B; 2 days

90–97; 280–281(dec.); (EtOH); lit. (77)f 281–221

8

B; 5 days

90–95; 203–205; (EtOH) –

9

B; 3 months

83; 246–248; (see Ref. 22); lit. (91)g 246–2483a; (56–64)f,

22

10

D (slow addition); 4 hours

73; 147–149; (EtOH/H2O); lit. (67)h 147–14813

a

Representative spectroscopic and analytical data are included in reference 19. Methods (for experimental quantities see the text, all reactions were performed at room temperature on a 10–100 mmol scale): A, a solution of KICl2 (generally 2 equiv. of a 1 or 2 molar solution) was added to a solution or suspension of the