Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2005(4): 547-550
DOI: 10.1055/s-2005-861791
DOI: 10.1055/s-2005-861791
PAPER
© Georg Thieme Verlag Stuttgart · New York
The Conversion of Phenols to the Corresponding Aryl Halides Under Mild Conditions
Further Information
Received
23 July 2004
Publication Date:
18 January 2005 (online)
Publication History
Publication Date:
18 January 2005 (online)

Abstract
Mild, novel procedures have been developed for the syntheses of aryl halides from the corresponding phenols in modest to good yields via boronate ester intermediates.
Key words
aryl halides - phenols - boronates - halogenation - palladium coupling
- 1
Johnson MR.Melvin LS. In Cannabinoids as Therapeutic AgentsMechoulam R. CRC Press; Boca Raton: 1986. p.121-145 - 2
Huffman JW.Liddle J.Yu S.Aung MM.Abood ME.Wiley JL.Martin BR. Bioorg. Med. Chem. 1999, 7: 2095 - 3 Thompson, A. L. S., unpublished work.
-
4a
Dominianni SJ.Ryan CW.De Armitt CW. J. Org. Chem. 1977, 42: 344 -
4b
Huffman JW.Joyner HH.Lee MD.Jordan RD.Pennington WT. J. Org. Chem. 1991, 56: 2081 -
5a
Bay E.Bak DA.Timony PE.Leone-Bay A. J. Org. Chem. 1990, 55: 3415 -
5b
Bestman HJ.Schnabel KH. Justus Liebigs Ann. Chem. 1966, 698: 106 -
5c
Wiley GA.Hershkowitz RL.Rein BM.Chung BC. J. Am. Chem. Soc. 1964, 86: 964 -
5d
Albert A.Clarke J. J. Chem. Soc. 1964, 1666 -
5e
Park JD.Rosser RW.Lacher JR. J. Org. Chem. 1962, 27: 1462 -
5f
Cramer R.Coffman DD. J. Org. Chem. 1961, 26: 4164 -
5g
Price CC.Roberts EM. Org. Synth. Coll. Vol III Wiley; New York: 1955. p.272 -
5h
Bendich A.Russell PJ.Fox JJ. J. Am. Chem. Soc. 1954, 76: 6073 -
5i
Surrey AR.Cutler RA. J. Am. Chem. Soc. 1954, 76: 1109 -
5j
Baddiley J.Topham A. J. Chem. Soc. 1944, 678 - 6
Murata M.Oyama T.Watanabe W.Masuda Y. J. Org. Chem. 2000, 65: 164 - 7
Kabalka GW.Akula MR.Zhang J. Nucl. Med. Biol. 2002, 29: 841 - 8
Kabalka GW.Sastry KAR.Sastry U.Somayaji V. Org. Prep. Proced. Int. 1982, 14: 359 - 10
Nesmejanow AN.Perewalowa EG.Jurjewa LP. Chem. Ber. 1960, 2729 - For selected examples of experimental methods for the preparation of trifluoromethanesulfonates, see:
-
11a
Ritter K. Synthesis 1993, 735 -
11b
Stang PJ.Hanack M.Subramanian LR. Synthesis 1982, 85 -
11c
Echavarren AM.Stille JK. J. Am. Chem. Soc. 1987, 109: 5478 -
11d
Tilley JW.Danho W.Lovey K.Wagner R.Swistok J.Makofske R.Michalewsky J.Triscari J.Nelson D.Weatherford S. J. Med. Chem. 1991, 34: 1125 -
11e
Rudisill DE.Stille JK. J. Org. Chem. 1989, 54: 5856 - 12
Kaliakoudas D.Eugster CH.Ruedi P. Helv. Chim. Acta 1990, 73: 48 -
13a
Harayama T.Nakatsuka K.Nishioka H.Murakami K.Hayashida N.Ishii H. Chem. Pharm. Bull. 1994, 42: 2170 -
13b
Mitteilung K.Reisch J.Rosenthal BHW. Monatsh. Chem. 1987, 118: 871 - 14
Sukman EL. inventors; U.S. Patent, 4264593. ; no spectroscopic data are included in this patent - 15
Barluenga J.Campos PJ.Gonzalez JM.Asensio G. J. Chem. Soc, Perkin Trans. 1 1984, 2623
References
Pinacolboronates 6 could be converted to the corresponding boronic acid using NaIO4 and NH4OAc. The boronic acids were then converted to the aryl bromide under the conditions described in ref.7 The overall yields for this procedure were inferior to those developed subsequently.