Site-Selective N-Arylation of Carbazoles with Halogenated Fluorobenzenes

Lei Wang; Enhui Ji; Ning Liu; Bin Dai

doi:10.1055/s-0035-1560386

Synthesis, Inhaltsverzeichnis

Synthesis 2016; 48(05): 737-750
DOI: 10.1055/s-0035-1560386

paper

Site-Selective N-Arylation of Carbazoles with Halogenated Fluorobenzenes

Lei Wang

School of Chemistry and Chemical Engineering, Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University, North 4th Road, Shihezi, Xinjiang 832003, P. R. of China eMail: ninglau@163.com eMail: dbinly@126.com

,

Enhui Ji

School of Chemistry and Chemical Engineering, Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University, North 4th Road, Shihezi, Xinjiang 832003, P. R. of China eMail: ninglau@163.com eMail: dbinly@126.com

,

Ning Liu*

School of Chemistry and Chemical Engineering, Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University, North 4th Road, Shihezi, Xinjiang 832003, P. R. of China eMail: ninglau@163.com eMail: dbinly@126.com

,

Bin Dai*

School of Chemistry and Chemical Engineering, Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University, North 4th Road, Shihezi, Xinjiang 832003, P. R. of China eMail: ninglau@163.com eMail: dbinly@126.com

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

A method for the highly site-selective C–N bond-formation reaction of halogenated fluorobenzenes with carbazoles is described. The selectivity of iodine and fluorine atoms on the aromatic ring of fluorinated iodobenzenes was initially determined with a copper–N,N-diisopropylethylamine catalytic system. By changing the position of the iodine atom on the aromatic ring from the 3- or 4-position to the 2-position, the preferred coupling site was switched from the iodine atom to the fluorine atom. Steric hindrance of the fluorinated iodobenzenes is responsible for the selectivity switch. After elucidating the reaction mechanisms of these reaction processes, a metal-free method for the highly site-selective C–N bond-formation reaction of halogenated fluorobenzenes with carbazoles was revealed through C–F bond activation. The metal-free system is able to handle a range of halogenated groups. Thus, a broad range of chlorinated, brominated, and iodinated N-arylated carbazoles were generated, which are widely useful in organic chemistry.

Key words

N-arylation - site selectivity - halobenzenes - N-arylated carbazoles

Volltext

Referenzen

References

1a Choi TA, Czerwonka R, Fröhner W, Krahl MP, Reddy KR, Franzblau SG, Knölker H.-J. ChemMedChem 2006; 1: 812
1b Choi TA, Czerwonka R, Forke R, Jäger A, Knöll J, Krahl MP, Krause T, Reddy KR, Franzblau SG, Knölker H.-J. Med. Chem. Res. 2008; 17: 374
1c Kimura T, Hosokawa-Muto J, Asami K, Murai T, Kuwata K. Eur. J. Med. Chem. 2011; 46: 5675
1d Zall A, Kieser D, Höttecke N, Naumann EC, Thomaszewski B, Schmidt B. Bioorg. Med. Chem. 2011; 19: 4903
1e Bandgar BP, Adsul LK, Chavan HV, Jalde SS, Shringare SN, Masand V. Bioorg. Med. Chem. Lett. 2012; 22: 5839
1f Zhu D, Chen M, Li M, Luo B, Zhao Y, Huang P, Xue F, Rapposelli S, Pi R, Wen S. Eur. J. Med. Chem. 2013; 68: 81

2a Thomas KR. J, Lin JT, Tao YT, Ko CW. J. Am. Chem. Soc. 2001; 123: 9404
2b Wong WY, Ho CL, Gao ZQ, Mi BX, Chen CH, Cheah KW, Lin ZY. Angew. Chem. Int. Ed. 2006; 45: 7800
2c Teng C, Yang XC, Yuan CZ, Li CY, Chen RK, Tian HN, Li SF, Hagfeldt A, Sun LC. Org. Lett. 2009; 11: 5542
2d Tang J, Hua JL, Wu WJ, Li J, Jin ZG, Long YT, Tian H. Energy Environ. Sci. 2010; 3: 1736
2e Song BJ, Song HM, Choi IT, Kim SK, Seo KD, Kang MS, Lee MJ, Cho DW, Ju MJ, Kim HK. Chem. Eur. J. 2011; 17: 11115
2f Wang Y, Chen B, Wu W, Li X, Zhu W, Tian H, Xie Y. Angew. Chem. Int. Ed. 2014; 53: 10779
2g Tan L.-L, Xie L.-J, Shen Y, Liu J.-M, Xiao L.-M, Kuang D.-B, Su C.-Y. Dyes Pigm. 2014; 100: 269
2h Adhikari RM, Mondal R, Shah BK, Neckers DC. J. Org. Chem. 2007; 72: 4727
2i Kwak J, Lyu YY, Lee H, Choi B, Char K, Lee C. J. Mater. Chem. 2012; 22: 6351

3a Berger R, Resnati G, Metrangolo P, Weber E, Hulliger J. Chem. Soc. Rev. 2011; 40: 3496
3b Schneider H.-J. Chem. Sci. 2012; 3: 1381
3c Pan J.-H, Chou Y.-M, Chiu H.-L, Wang B.-C. Aust. J. Chem. 2009; 62: 483
3d Zhu C.-C, Guo K.-P, Guo W.-B, Liu W.-B, He Y.-B, Li Z.-M, Gao X.-C, Deng F.-J, Wei B. Opt. Mater. 2013; 35: 2095
3e Ho C.-L, Wong W.-Y, Yao B, Xie Z, Wang L, Lin Z. J. Organomet. Chem. 2009; 694: 2735
3f Ho C.-L, Wang Q, Lam C.-S, Wong W.-Y, Ma D, Wang L, Gao Z.-Q, Chen C.-H, Cheah K.-W, Lin Z. Chem. Asian J. 2009; 4: 89
3g Wei B, Liu J.-Z, Zhang Y, Zhang J.-H, Peng H.-N, Fan H.-L, He Y.-B, Gao X.-C. Adv. Funct. Mater. 2010; 20: 2448

4a Müller K, Faeh C, Diederich F. Science 2007; 317: 1881
4b Purser S, Moore PR, Swallow S, Gouverneur V. Chem. Soc. Rev. 2008; 37: 320
4c Isanbor C, O’Hagan D. J. Fluorine Chem. 2006; 127: 303
4d Hagmann WK. J. Med. Chem. 2008; 51: 4359
4e Kirk KL. Org. Process Res. Dev. 2008; 12: 305

5a Ullmann F. Ber. Dtsch. Chem. Ges. 1903; 36: 2382
5b Ullmann F, Illgen E. Ber. Dtsch. Chem. Ges. 1914; 47: 380

6a Nozaki K, Takahashi K, Nakano K, Hiyama T, Tang H.-Z, Fujiki M, Yamaguchi S, Tamao K. Angew. Chem. Int. Ed. 2003; 42: 2051
6b Kitawaki T, Hayashi Y, Ueno A, Chida N. Tetrahedron 2006; 62: 6792
6c Ackermann L, Althammer A. Angew. Chem. Int. Ed. 2007; 46: 1627
6d Zhou Y, Verkade JG. Adv. Synth. Catal. 2010; 352: 616

7 Riedmüller S, Nachtsheim BJ. Beilstein J. Org. Chem. 2013; 9: 1202
8 Zhu D, Liu Q, Luo B, Chen M, Pi R, Huang P, Wen S. Adv. Synth. Catal. 2013; 355: 2172
9 Guo F, Wang L, Wang P, Yu J, Han J. Asian J. Org. Chem. 2012; 1: 218

10a Guram AS, Buchwald SL. J. Am. Chem. Soc. 1994; 116: 7901
10b Wolfe JP, Wagaw S, Buchwald SL. J. Am. Chem. Soc. 1996; 118: 7215
10c Wolfe JP, Wagaw S, Marcoux J, Buchwald SL. Acc. Chem. Res. 1998; 31: 805
10d Yang BH, Buchwald SL. J. Organomet. Chem. 1999; 576: 125
10e Muci AR, Buchwald SL. Top. Curr. Chem. 2002; 219: 131
10f Anderson KW, Tundel RE, Ikawa T, Altman RA, Buchwald SL. Angew. Chem. Int. Ed. 2006; 45: 6523

11a Hartwig JF. Angew. Chem. Int. Ed. 1998; 37: 2046
11b Hartwig JF. Acc. Chem. Res. 1998; 31: 852
11c Hartwig JF. Pure Appl. Chem. 1999; 71: 1417
11d Hartwig JF. Synlett 1997; 329
11e Baranano D, Mann G, Hartwig JF. Curr. Org. Chem. 1997; 1: 287

12a Ma DW, Zhang YD, Yao JC, Wu SH, Tao FG. J. Am. Chem. Soc. 1998; 120: 12459
12b Zhang H, Cai Q, Ma DW. J. Org. Chem. 2005; 70: 5164
12c Ma DW, Cai Q. Acc. Chem. Res. 2008; 41: 1450
12d Ley SV, Thomas AW. Angew. Chem. Int. Ed. 2003; 42: 5400
12e Carril M, SanMartin R, Domínguez E. Chem. Soc. Rev. 2008; 37: 639
12f Monnier F, Taillefer M. Angew. Chem. Int. Ed. 2009; 48: 6954
12g Rao H.-H, Fu H. Synlett 2011; 745
12h Chemler SR. Science 2013; 341: 624
12i Chen F, Liu N, Ji E, Dai B. RSC Adv. 2015; 5: 51512

13a Klapars A, Antilla JC, Huang XH, Buchwald SL. J. Am. Chem. Soc. 2001; 123: 7727
13b Surry DS, Buchwald SL. Chem. Sci. 2010; 1: 13

14a He M, Soulé J.-F, Doucet H. ChemCatChem 2014; 6: 1824
14b Yan T, Zhao L, He M, Soulé J.-F, Bruneau C, Doucet H. Adv. Synth. Catal. 2014; 356: 1586
14c He M, Soulé J.-F, Doucet H. ChemCatChem 2015; 7: 2130

15 Huo Z, Li Z, Wang T, Zeng H. Tetrahedron 2013; 69: 8964
16 Maligres PE, Krska SW, Dormer PG. J. Org. Chem. 2012; 77: 7646
17 Kim MK, Kwon J, Kwon T.-H, Hong J.-I. New J. Chem. 2010; 34: 1317
18 Lee DH, Lee SG, Jung DI, Hahn JT. Asian J. Chem. 2013; 25: 501
19 Son HS, Lee JY. Org. Electron. 2011; 12: 1025
20 Kwon JK, Cho JH, Ryu Y.-S, Oh SH, Yum EK. Tetrahedron 2011; 67: 4820
21 Liu Y, Nishiura M, Wang Y, Hou Z. J. Am. Chem. Soc. 2006; 128: 5592
22 Zhu D, Liu Q, Luo B, Chen M, Pi R, Huang P, Wen S. Adv. Synth. Catal. 2013; 355: 2172
23 Kautny P, Lumpi D, Wang Y, Tissot A, Bintinger J, Horkel E, Stöger B, Hametner C, Hagemann H, Ma D, Fröhlich J. J. Mater. Chem. C 2014; 2: 2069
24 Liu L, Wong W.-Y, Shi J.-X, Cheah KW, Lee T.-H, Leung LM. J. Organomet. Chem. 2006; 691: 4028
25 Chen Y.-C, Huang G.-S, Hsiao C.-C, Chen S.-A. J. Am. Chem. Soc. 2006; 128: 8549
26 Park JH, Koh TW, Do Y, Lee MH, Yoo S. J. Polym. Sci., Part A: Polym. Chem. 2012; 50: 2356
27 Jian H, Tour JM. J. Org. Chem. 2003; 68: 5091

Zusatzmaterial

Supporting Information