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-00000083.xml
Synlett 2006(12): 1965-1967
DOI: 10.1055/s-2006-948162
DOI: 10.1055/s-2006-948162
LETTER
© Georg Thieme Verlag Stuttgart · New York
Efficient Synthesis of 2-Substituted Imidazoles by Palladium-Catalyzed Cross-Coupling with Benzylzinc Reagents
Further Information
Received
28 March 2006
Publication Date:
24 July 2006 (online)
Publication History
Publication Date:
24 July 2006 (online)
![](https://www.thieme-connect.de/media/synlett/200612/lookinside/thumbnails/10.1055-s-2006-948162-1.jpg)
Abstract
Substituted benzylzinc reagents have been used in novel cross-coupling reactions with 2-iodo imidazoles to form compounds containing both a phenol and an imidazole moiety. The intramolecular hydrogen-bonding properties of these compounds were subsequently studied.
Key words
cross-coupling - palladium - zinc - benzylation - heterocycles
- 1
Pesavento RP.Van Der Donk WA. Adv. Protein Chem. 2001, 58: 317 ; and references cited therein - 2
Stryer L. Biochemistry 5th ed.: W. H. Freeman and Company; New York: 1995. - 3
Hays A.-MA.Vassiliev IR.Golbeck JH.Debus RJ. Biochemistry 1999, 38: 11851 - 5
Frutos RP.Gallou I.Reeves D.Xu Y.Krishnamurthy D.Senanayake CH. Tetrahedron Lett. 2005, 46: 8369 ; and references cited therein - 6
Abbotto A.Bradamante S.Pagani GA. J. Org. Chem. 1996, 61: 1761 - 7
Abarca-Gonzalez B.Jones RA.Medio-Simon M.Quilez-Pardo J.Sepulveda-Arques J.Zaballos-Garcia E. Synth. Commun. 1990, 20: 321 - 8
Moreno-Manas M.Bassa J.Llado N.Pleixats R. J. Heterocycl. Chem. 1990, 27: 673 - 9
Murahashi S.-I. J. Organomet. Chem. 2002, 653: 27 - 10
Negishi E.Zeng X.Tan Z.Qian M.Hu Q.Huang Z. In Metal-Catalyzed Cross-Coupling Reactions 2nd ed., Vol. 2:de Meijere A.Diederich F. Wiley-VCH; Weinheim: 2004. p.815-889 - 11
Knochel P.Singer RD. Chem. Rev. 1993, 93: 2117 - 12
Angiolelli ME.Casalnuovo AL.Selby TP. Synlett 2000, 905 - 14
Prasad ASB.Stevenson TM.Citineni JR.Nyzam V.Knochel P. Tetrahedron 1997, 53: 7237 - 15
Reiter LA.Mitchell PG.Martinelli GJ.Lopresti-Morrow LL.Yocum SA.Eskra JD. Bioorg. Med. Chem. Lett. 2003, 13: 2331
References and Notes
The calculations will be reported separately together with further analyses of the target compounds.
13This reagent is also commercially available from Aldrich.
16Compound 9c was not deprotected due to lack of material.