RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2009(16): 2818-2824
DOI: 10.1055/s-0029-1217406
DOI: 10.1055/s-0029-1217406
PSP
© Georg Thieme Verlag
Stuttgart ˙ New York
A Concise Synthesis of ortho-Iodobenzyl Alcohols via Addition of ortho-Iodophenyl Grignard Reagent to Aldehydes and Ketones
Weitere Informationen
Received
21 April 2009
Publikationsdatum:
22. Juni 2009 (online)
Publikationsverlauf
Publikationsdatum:
22. Juni 2009 (online)
Abstract
A wide range of both secondary and tertiary ortho-iodobenzyl alcohols was synthesized via addition of ortho-iodophenyl Grignard reagents to aldehydes and ketones. Significant improvements in terms of yields were observed with ketones upon addition of CeCl3. The potential application of the target compounds as precursors for novel electrophilic trifluoromethylating reagents based on hyper-valent iodine derivatives was demonstrated.
Key words
addition reactions - Grignard reactions - organometallic reagents - benzyl alcohols - hypervalent iodine compounds
-
1a
Metal-Catalyzed Cross-Coupling Reactions
de Meijere A.Diederich F. Wiley-VCH; Weinheim: 2004. -
1b
Transition
Metals for Organic Synthesis
Beller M.Bolm C. Wiley-VCH; Weinheim: 2004. - 2
Handbook
of Functionalized Organometallics
Knochel P. Wiley-VCH; Weinheim: 2005. -
3a
Eisenberger P.Gischig S.Togni A. Chem. Eur. J. 2006, 12: 2579 -
3b
Kieltsch I.Eisenberger P.Togni A. Angew. Chem. Int. Ed. 2007, 46: 754 -
3c
Eisenberger P.Kieltsch I.Armanino N.Togni A. Chem. Commun. 2008, 1575 -
3d
Kieltsch I.Eisenberger P.Stanek K.Togni A. Chimia 2008, 62: 260 -
3e
Stanek K.Koller R.Togni A. J. Org. Chem. 2008, 73: 7678 -
3f
Koller R.Stanek K.Stolz D.Aardoom R.Niedermann K.Togni A. Angew. Chem. Int. Ed. 2009, 48: 4332 -
4a
Merkushev EB. Synthesis 1988, 923 -
4b
Hanson JR. J. Chem. Res., Synop. 2006, 277 -
4c
Stavber S.Jereb M.Zupan M. Synthesis 2008, 1487 -
5a
Meyer N.Seebach D. Chem. Ber. 1980, 113: 1304 -
5b
Perozzi EF.Michalak RS.Figuly GD.Stevenson WH.Dess D.Ross MR.Martin JC. J. Org. Chem. 1981, 46: 1049 -
5c
Dolenc D.Plesnicar B. J. Org. Chem. 2006, 71: 8028 -
5d
Usui S.Hashimoto Y.Morey JV.Wheatley AEH.Uchiyama M. J. Am. Chem. Soc. 2007, 129: 15102 -
5e
Clososki GC.Rohbogner CJ.Knochel P. Angew. Chem. Int. Ed. 2007, 46: 7681 - 6
Logullo FM.Seitz AH.Friedman L. Org. Synth. Coll. Vol. 5 Wiley; New York: 1973. p.54 -
7a
Nicolaou KC.Dai WM.Hong YP.Baldridge KK.Siegel JS.Tsay SC. J. Am. Chem. Soc. 1993, 115: 7944 -
7b
Wisniewski GJ.Klingberg D.Huang D.Slattery BJ. J. Org. Chem. 1997, 62: 603 -
7c
Martín-Matute B.Nevado C.Cárdenas DJ.Echavarren AM. J. Am. Chem. Soc. 2003, 125: 5757 -
8a
Surry DS.Su X.Fox DJ.Franckevicius V.Macdonald SJF.Spring DR. Angew. Chem. Int. Ed. 2005, 44: 1870 -
8b
Krasovskiy A.Tishkov A.del Amo V.Mayr H.Knochel P. Angew. Chem. Int. Ed. 2006, 45: 5010 -
8c
Al-Zoubi RM.Marion O.Hall DG. Angew. Chem. Int. Ed. 2008, 47: 2876 - For similar approaches, see:
-
9a
Krasovskiy A.Knochel P. Angew. Chem. Int. Ed. 2004, 43: 3333 -
9b
Boymond L.Rottländer M.Cahiez G.Knochel P. Angew. Chem. Int. Ed. 1998, 37: 1701 -
10a
Trost BM.Pearson WH. J. Am. Chem. Soc. 1981, 103: 2483 -
10b
Slocum DW.Moon R.Thompson J.Coffey DS.Li JD.Slocum MG. Tetrahedron Lett. 1994, 35: 385 -
10c
Dunne JP.Bockmeyer M.Tacke M. Eur. J. Inorg. Chem. 2003, 458 - 11
Charette AB.Mellon C. Tetrahedron 1998, 54: 10525 - 12
Amey RL.Martin JC. J. Org. Chem. 1979, 44: 1779 - 13
Chen C.-A.Wu K.-H.Gau H.-M. Angew. Chem. Int. Ed. 2007, 46: 5373 - 14
Mintz MJ.Walling C. Org. Synth. Coll. Vol. 5 Wiley; New York: 1973. p.84