Abstract
A simple and effective procedure for conversion of primary, secondary, allylic and benzylic alcohols into the corresponding iodides is described using NaI/Amberlyst 15 in acetonitrile at room temperature. Selective conversion of benzylic alcohols in the presence of saturated alcohols into the corresponding benzylic iodides is achieved under these conditions.
Key words
iodination - Amberlyst 15 - benzylic alcohol - saturated alcohol - iodides
References
1a
Bohlmann R. In Comprehensive Organic Synthesis
Vol. 6:
Trost BM.
Fleming I.
Pergamon Press;
Oxford:
1991.
p.203-223
1b
Hudlicky M.
Hudlicky T. In
The Chemistry of Functional Groups, Supplement D
Patai S.
Rappoport Z.
Wiley;
New York:
1983.
p.1021
1c
Chambers RD.
James SR. In Comprehensive Organic Chemistry
Vol. 1:
Barton D.
Ollis WD.
Pergamon Press;
Oxford:
1979.
p.493-575
1d
Su MD.
Chu SY.
J. Am. Chem. Soc.
1999,
121:
1045
2
Wakefield BJ.
In Organolithium Methods
Academic Press;
London:
1988.
3
Marsden SP.
Contemp. Org. Synth.
1997,
4:
118 ; and references cited therein
4
Villieras J.
Bacquet C.
Normant JF.
Bull. Chem. Soc. Fr.
1975,
1797
5a
Landauer SR.
Rydon HN.
J. Chem. Soc.
1953,
2224
5b
Coe DG.
Landauer SR.
Rydon HN.
J. Chem. Soc.
1954,
2281
5c
Rydon HN.
Tonge BL.
J. Chem. Soc.
1956,
3043
6a
Crofts PC.
Downie IM.
J. Chem. Soc.
1963,
2559
6b
Lee JB.
Nolan TJ.
Can. J. Chem.
1966,
44:
1331
6c
Haylock CR.
Melton LD.
Slessor KN.
Tracey AS.
Carbohydr. Res.
1971,
16:
375
6d
Verheyden JPH.
Moffatt JG.
J. Org. Chem.
1972,
37:
2289
7
Hanessian S.
Ponpipom MM.
Lavallee P.
Carbohydr. Res.
1972,
24:
45
8a
Garegg PJ.
Samuelsson B.
J. Chem. Soc., Perkin Trans. 1
1980,
2866
8b
Garegg PJ.
Johansson R.
Ortega C.
Samuelsson B.
J. Chem. Soc., Perkin Trans. 1
1982,
681
9
Jung ME.
Ornstein PL.
Tetrahedron Lett.
1977,
2659
10
Jung ME.
Hatfield GL.
Tetrahedron Lett.
1978,
4483
11a
Morita T.
Yoshida S.
Okamoto Y.
Sakurai H.
Synthesis
1979,
379
11b
Olah GA.
Narang SC.
Gupta BGB.
Malhotra R.
J. Org. Chem.
1979,
44:
1247
12
Olah GA.
Narang SC.
Gupta BGB.
Malhotra R.
Angew. Chem., Int. Ed. Engl.
1979,
18:
612
13
Lauwers M.
Regnier B.
Van Eenoo M.
Denis JN.
Krief A.
Tetrahedron Lett.
1979,
1801
14
Reddy CK.
Periasamy M.
Tetrahedron Lett.
1989,
30:
5663
15
Deo MD.
Marcantoni E.
Torregiani E.
Bartoli G.
Bellucci MC.
Bosco M.
Sambri L.
J. Org. Chem.
2000,
65:
2830
16
Kad GL.
Kaur J.
Bansal P.
Singh J.
J. Chem. Res., Synop.
1996,
188
17
Bandgar BP.
Sadavarte VS.
Bettigeri SV.
Monatsh. Chem.
2002,
133:
345
18
Olah GA.
Hussain A.
Singh BP.
Mehrotra AK.
J. Org. Chem.
1983,
48:
3667
19
Mandal AK.
Mahajan SW.
Tetrahedron Lett.
1985,
26:
3863
20
Vankar YD.
Rao CT.
Tetrahedron Lett.
1985,
26:
2717
21
Classon B.
Liu Z.
Samuelsson B.
J. Org. Chem.
1988,
53:
6126
22
Joseph R.
Pallan PS.
Sudalai A.
Ravindranathan T.
Tetrahedron Lett.
1995,
36:
609
23
Ponde D.
Borade HB.
Sudalai A.
Ravindranathan T.
Deshpande VH.
Tetrahedron Lett.
1996,
37:
4605 ; and references cited therein
24
General Procedure for the Conversion of Alcohols to Iodides (Table 1). To a stirred suspension of alcohol (1 mmol) and NaI (0.150 g, 1 mmol) in MeCN (10 mL) was added amberlyst 15 (H+-form, 1 g), and the resulting mixture was stirred at r.t. After completion of the reaction (TLC or GC), Et2O (10 mL) was added and washed with aq sat. NaHCO3 solution, followed by NaHSO4. The resultant organic layer was extracted with Et2O (3 × 10 mL) and the combined extract dried over anhyd Na2SO4. The solvent was removed under reduced pressure to afford iodides in almost pure form. If necessary, products were purified by column chromatography (eluent: hexane-EtOAc). The products were identified by IR, 1H NMR, and GC.
25a
Vogel A.
Vogel"s Textbook of Practical Organic Chemistry
4th ed.:
Longman;
Essex, UK:
1978.
25b
Dictionary of Organic Compounds
6th ed.:
Chapman and Hall;
London:
1995.
