Iron(II) bromide-catalyzed intramolecular C-H bond amination [1,2]-shift tandem reactions of aryl azides

doi:10.1021/ja3113565

. 2013 Jan 16;135(2):620-3.

doi: 10.1021/ja3113565. Epub 2013 Jan 3.

Iron(II) bromide-catalyzed intramolecular C-H bond amination [1,2]-shift tandem reactions of aryl azides

Quyen Nguyen¹, Tuyen Nguyen, Tom G Driver

Affiliations

PMID: 23265139
PMCID: PMC3622273
DOI: 10.1021/ja3113565

Iron(II) bromide-catalyzed intramolecular C-H bond amination [1,2]-shift tandem reactions of aryl azides

Quyen Nguyen et al. J Am Chem Soc. 2013.

. 2013 Jan 16;135(2):620-3.

doi: 10.1021/ja3113565. Epub 2013 Jan 3.

Authors

Quyen Nguyen¹, Tuyen Nguyen, Tom G Driver

Affiliation

¹ Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL 60607-7061, USA.

PMID: 23265139
PMCID: PMC3622273
DOI: 10.1021/ja3113565

Abstract

Iron(II) bromide catalyzes the transformation of ortho-substituted aryl azides into 2,3-disubstituted indoles through a tandem ethereal C-H bond amination [1,2]-shift reaction. The preference for the 1,2-shift component of the tandem reaction was established to be Me < 1° < 2° < Ph.

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Figures

**Scheme 1**
Observation of a Fe(II)-promoted Tandem Reaction.

**Scheme 2**
Possible Mechanisms for Fe-Catalyzed Tandem Reaction.

**Scheme 3**
Isolation of Reactive Intermediates.

See this image and copyright information in PMC

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References

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1. For recent reviews of C–H bond amination, see: Davies HML, Manning JR. Nature. 2008;451:417.Collet F, Dodd RH, Dauban P. Chem Commun. 2009:5061.Driver TG. Org Biomol Chem. 2010;8:3831.Du Bois J. Org Process Res Dev. 2011;15:758.Davies HML, Du Bois J, Yu JQ. Chem Soc Rev. 2011;40:1855.Roizen JL, Harvey ME, Du Bois J. Acc Chem Res. 2012;45:911.
1. For leading reports of N-atom transfer, see: Espino CG, Du Bois J. Angew Chem, Int Ed. 2001;40:598.Espino CG, Fiori KW, Kim M, Du Bois J. J Am Chem Soc. 2004;126:15378.Lebel H, Huard K, Lectard S. J Am Chem Soc. 2005;127:14198.Fraunhoffer KJ, White MC. J Am Chem Soc. 2007;129:7274.Liang C, Collet F, Robert-Peillard F, Müller P, Dodd RH, Dauban P. J Am Chem Soc. 2008;130:343.Reed SA, White MC. J Am Chem Soc. 2008;130:3316.Milczek E, Boudet N, Blakey S. Angew Chem, Int Ed. 2008;47:6825.Nguyen AI, Zarkesh RA, Lacy DC, Thorson MK, Heyduk AF. Chem Sci. 2011;2:166.
1. Tsang WCP, Zheng N, Buchwald SL. J Am Chem Soc. 2005;127:14560. - PubMed
2. Thu HY, Yu WY, Che CM. J Am Chem Soc. 2006;128:9048. - PubMed
3. Mei TS, Wang X, Yu JQ. J Am Chem Soc. 2009;131:10806. - PubMed
4. Tan Y, Hartwig JF. J Am Chem Soc. 2010;132:3676. - PubMed
5. Kim JY, Park SH, Ryu J, Cho SH, Kim SH, Chang S. J Am Chem Soc. 2012;134:9110. - PubMed

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[1] For recent, leading reviews, see: Wasilke JC, Obrey SJ, Baker RT, Bazan GC. Chem Rev. 2005;105:1001.Nicolaou KC, Edmonds DJ, Bulger PG. Angew Chem, Int Ed. 2006;45:7134.Padwa A. J Org Chem. 2009;74:6421.Grant TN, Rieder CJ, West FG. Chem Commun. 2009:5676.Touré BB, Hall DG. Chem Rev. 2009;109:4439.Lu LQ, Chen JR, Xiao WJ. Acc Chem Res. 2012;45:1278.

[2] For recent, leading reviews, see: Wasilke JC, Obrey SJ, Baker RT, Bazan GC. Chem Rev. 2005;105:1001.Nicolaou KC, Edmonds DJ, Bulger PG. Angew Chem, Int Ed. 2006;45:7134.Padwa A. J Org Chem. 2009;74:6421.Grant TN, Rieder CJ, West FG. Chem Commun. 2009:5676.Touré BB, Hall DG. Chem Rev. 2009;109:4439.Lu LQ, Chen JR, Xiao WJ. Acc Chem Res. 2012;45:1278.

[3] For recent reports, cf. Green JC, Pettus TRR. J Am Chem Soc. 2010;133:1603.Zou YQ, Lu LQ, Fu L, Chang NJ, Rong J, Chen JR, Xiao WJ. Angew Chem, Int Ed. 2011;50:7171.Tietze LF, Hungerland T, Düfert A, Objartel I, Stalke D. Chem Eur J. 2012;18:3286.Okazaki E, Okamoto R, Shibata Y, Noguchi K, Tanaka K. Angew Chem, Int Ed. 2012;51:6722.Jansone-Popova S, May JA. J Am Chem Soc. 2012;134:17877.

[4] For recent reports, cf. Green JC, Pettus TRR. J Am Chem Soc. 2010;133:1603.Zou YQ, Lu LQ, Fu L, Chang NJ, Rong J, Chen JR, Xiao WJ. Angew Chem, Int Ed. 2011;50:7171.Tietze LF, Hungerland T, Düfert A, Objartel I, Stalke D. Chem Eur J. 2012;18:3286.Okazaki E, Okamoto R, Shibata Y, Noguchi K, Tanaka K. Angew Chem, Int Ed. 2012;51:6722.Jansone-Popova S, May JA. J Am Chem Soc. 2012;134:17877.

[5] For recent reviews of C–H bond amination, see: Davies HML, Manning JR. Nature. 2008;451:417.Collet F, Dodd RH, Dauban P. Chem Commun. 2009:5061.Driver TG. Org Biomol Chem. 2010;8:3831.Du Bois J. Org Process Res Dev. 2011;15:758.Davies HML, Du Bois J, Yu JQ. Chem Soc Rev. 2011;40:1855.Roizen JL, Harvey ME, Du Bois J. Acc Chem Res. 2012;45:911.

[6] For recent reviews of C–H bond amination, see: Davies HML, Manning JR. Nature. 2008;451:417.Collet F, Dodd RH, Dauban P. Chem Commun. 2009:5061.Driver TG. Org Biomol Chem. 2010;8:3831.Du Bois J. Org Process Res Dev. 2011;15:758.Davies HML, Du Bois J, Yu JQ. Chem Soc Rev. 2011;40:1855.Roizen JL, Harvey ME, Du Bois J. Acc Chem Res. 2012;45:911.

[7] For leading reports of N-atom transfer, see: Espino CG, Du Bois J. Angew Chem, Int Ed. 2001;40:598.Espino CG, Fiori KW, Kim M, Du Bois J. J Am Chem Soc. 2004;126:15378.Lebel H, Huard K, Lectard S. J Am Chem Soc. 2005;127:14198.Fraunhoffer KJ, White MC. J Am Chem Soc. 2007;129:7274.Liang C, Collet F, Robert-Peillard F, Müller P, Dodd RH, Dauban P. J Am Chem Soc. 2008;130:343.Reed SA, White MC. J Am Chem Soc. 2008;130:3316.Milczek E, Boudet N, Blakey S. Angew Chem, Int Ed. 2008;47:6825.Nguyen AI, Zarkesh RA, Lacy DC, Thorson MK, Heyduk AF. Chem Sci. 2011;2:166.

[8] For leading reports of N-atom transfer, see: Espino CG, Du Bois J. Angew Chem, Int Ed. 2001;40:598.Espino CG, Fiori KW, Kim M, Du Bois J. J Am Chem Soc. 2004;126:15378.Lebel H, Huard K, Lectard S. J Am Chem Soc. 2005;127:14198.Fraunhoffer KJ, White MC. J Am Chem Soc. 2007;129:7274.Liang C, Collet F, Robert-Peillard F, Müller P, Dodd RH, Dauban P. J Am Chem Soc. 2008;130:343.Reed SA, White MC. J Am Chem Soc. 2008;130:3316.Milczek E, Boudet N, Blakey S. Angew Chem, Int Ed. 2008;47:6825.Nguyen AI, Zarkesh RA, Lacy DC, Thorson MK, Heyduk AF. Chem Sci. 2011;2:166.

[9] Tsang WCP, Zheng N, Buchwald SL. J Am Chem Soc. 2005;127:14560. - PubMed

Thu HY, Yu WY, Che CM. J Am Chem Soc. 2006;128:9048. - PubMed

Mei TS, Wang X, Yu JQ. J Am Chem Soc. 2009;131:10806. - PubMed

Tan Y, Hartwig JF. J Am Chem Soc. 2010;132:3676. - PubMed

Kim JY, Park SH, Ryu J, Cho SH, Kim SH, Chang S. J Am Chem Soc. 2012;134:9110. - PubMed

[10] Tsang WCP, Zheng N, Buchwald SL. J Am Chem Soc. 2005;127:14560. - PubMed

[11] Thu HY, Yu WY, Che CM. J Am Chem Soc. 2006;128:9048. - PubMed

[12] Mei TS, Wang X, Yu JQ. J Am Chem Soc. 2009;131:10806. - PubMed

[13] Tan Y, Hartwig JF. J Am Chem Soc. 2010;132:3676. - PubMed

[14] Kim JY, Park SH, Ryu J, Cho SH, Kim SH, Chang S. J Am Chem Soc. 2012;134:9110. - PubMed

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Iron(II) bromide-catalyzed intramolecular C-H bond amination [1,2]-shift tandem reactions of aryl azides

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Iron(II) bromide-catalyzed intramolecular C-H bond amination [1,2]-shift tandem reactions of aryl azides

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