Palladium-Catalyzed N-Arylation of Amines and Amides with Aryltrimethylgermanes

Qiang Zhang; Cunfang Liu; Juan Shi; Qiong Xu; Lingxia Jin; Chaibin Zhao; Tianlei Zhang

doi:10.1055/s-0035-1562104

Synlett, Inhaltsverzeichnis

Synlett 2016; 27(13): 1945-1948
DOI: 10.1055/s-0035-1562104

letter

Palladium-Catalyzed N-Arylation of Amines and Amides with Aryltrimethylgermanes

Qiang Zhang*

School of Chemistry and Environmental Science, Shaanxi University of Technology, Shaanxi Province Key Laboratory of Catalytic Fundamentals & Applications, Hanzhong, 723001, P. R. of China eMail: zhangqiang22@126.com eMail: jinlingxia1982@126.com

,

Cunfang Liu

School of Chemistry and Environmental Science, Shaanxi University of Technology, Shaanxi Province Key Laboratory of Catalytic Fundamentals & Applications, Hanzhong, 723001, P. R. of China eMail: zhangqiang22@126.com eMail: jinlingxia1982@126.com

,

Juan Shi

School of Chemistry and Environmental Science, Shaanxi University of Technology, Shaanxi Province Key Laboratory of Catalytic Fundamentals & Applications, Hanzhong, 723001, P. R. of China eMail: zhangqiang22@126.com eMail: jinlingxia1982@126.com

,

Qiong Xu

School of Chemistry and Environmental Science, Shaanxi University of Technology, Shaanxi Province Key Laboratory of Catalytic Fundamentals & Applications, Hanzhong, 723001, P. R. of China eMail: zhangqiang22@126.com eMail: jinlingxia1982@126.com

,

Lingxia Jin*

School of Chemistry and Environmental Science, Shaanxi University of Technology, Shaanxi Province Key Laboratory of Catalytic Fundamentals & Applications, Hanzhong, 723001, P. R. of China eMail: zhangqiang22@126.com eMail: jinlingxia1982@126.com

,

Chaibin Zhao

School of Chemistry and Environmental Science, Shaanxi University of Technology, Shaanxi Province Key Laboratory of Catalytic Fundamentals & Applications, Hanzhong, 723001, P. R. of China eMail: zhangqiang22@126.com eMail: jinlingxia1982@126.com

,

Tianlei Zhang

School of Chemistry and Environmental Science, Shaanxi University of Technology, Shaanxi Province Key Laboratory of Catalytic Fundamentals & Applications, Hanzhong, 723001, P. R. of China eMail: zhangqiang22@126.com eMail: jinlingxia1982@126.com

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Abstract

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Abstract

Described herein is a novel palladium-catalyzed C–N bond-formation reaction employing aryltrimethylgermanes as the new arylating reagents. Primary/secondary amines or even amides could be smoothly arylated to provide the corresponding N-arylation products in moderate to excellent yields.

Key words

N-arylation - amine - amide - aryltrimethylgermane

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Referenzen

References and Notes

1a Lawrence SA. Amines: Synthesis, Properties, and Application. Cambridge University Press; Cambridge: 2004
1b Quan ML, Lam PY. S, Han Q, Pinto DJ. P, He MY, Li R, Ellis CD, Clark CG, Teleha CA, Sun J.-H, Alexander RS, Bai S, Luettgen JM, Knabb RM, Wong PC, Wexler RR. J. Med. Chem. 2005; 48: 1729
1c Barchéchath SD, Tawatao RI, Corr M, Carson DA, Cottam HB. J. Med. Chem. 2005; 48: 6409
1d Voets M, Antes I, Scherer C, Müller-Vieira U, Biemel K, Barassin C, Marchais-Oberwinkler S, Hartmann RW. J. Med. Chem. 2005; 48: 6632
1e Davey DD, Adler M, Arnaiz D, Eagen K, Erickson S, Guilford W, Kenrick M, Morrissey MM, Ohlmeyer M, Pan G, Paradkar VM, Parkinson J, Polokoff M, Saionz K, Santos C, Subramanyam B, Vergona R, Wei RG, Whitlow M, Ye B, Zhao ZS, Devlin JJ, Phillips G. J. Med. Chem. 2007; 50: 1146
1f Ullmann F. Ann. 1904; 232: 38
1g Fanta PE. Chem. Rev. 1946; 38: 139
1h Kwong FY, Klapars A, Buchwald SL. Org. Lett. 2002; 4: 581
1i Ma D, Cai Q, Zhang H. Org. Lett. 2003; 5: 2453

2a Hartwig JF. Palladium-Catalyzed Amination of Aryl Halides and Related Reactions in Handbook of Organopalladium Chemistry for Organic Synthesis. Vol. 1. Negishi EI. Wiley-Interscience; New York: 2002: 1051.2
2b Muci AR, Buchwald SL. Practical Palladium Catalysts for CAN and CAO Bond Formation. In Topics in Current Chemistry. Vol. 219. Miyaura N. Springer; Berlin: 2002: 133
2c Fagan PJ, Hauptman E, Shapiro R, Casalnuovo A. J. Am. Chem. Soc. 2000; 122: 5043
2d Rao KS, Wu T.-S. Tetrahedron 2012; 68: 7735
2e Lin B, Liu M, Ye Z, Ding J, Wu H, Cheng J. Org. Biomol. Chem. 2009; 7: 869

3a Wolfe JP, Wagaw S, Marcoux J.-F, Buchwald SL. Acc. Chem. Res. 1998; 31: 805
3b Hartwig JF. Angew. Chem. Int. Ed. 1998; 37: 2046

4a Kumari AS, Pathak DD. Tetrahedron Lett. 2015; 56: 4135
4b Quach TD, Batey RA. Org. Lett. 2003; 5: 4397
4c Poonam R, Rajendra S. Tetrahedron Lett. 2014; 55: 5256
4d Islam SM, Salam N, Mondal P, Roy AS, Ghosh K, Tuhinac K. J. Mol. Catal. A: Chem. 2014; 387: 7
4e Chan DM. T, Monaco KL, Wang RP, Winters MP. Tetrahedron Lett. 1998; 39: 2933
4f Batey RA, Quach TD. Org. Lett. 2003; 5: 4397
4g Kantam ML, Venkanna GT, Sridhar C, Sreedhar B, Choudary BM. J. Org. Chem. 2006; 71: 9522

5a Mitchell TN In Metal-Catalyzed Cross-Coupling Reactions. Vol. 1. de Mejijere A, Diederich F. Wiley-VCH; Weinheim: 2004: 125-162
5b Kwong FY, Klapars A, Buchwald SL. Org. Lett. 2002; 4: 581
5c Wolfe JP, Wagaw S, Marcoux J.-F, Buchwald SL. Acc. Chem. Res. 1998; 31: 805
5d Hartwig JF. Angew. Chem. Int. Ed. 1998; 37: 2046
5e Kumari AS, Pathak DD. Tetrahedron Lett. 2015; 56: 4135
5f Quach TD, Batey RA. Org. Lett. 2003; 5: 4397
5g Poonam R, Rajendra S. Tetrahedron Lett. 2014; 55: 5256
5h Batey RA, Quach TD. Org. Lett. 2003; 5: 4397

6 Anctil EJ. G, Snieckus V In Metal-Catalyzed Cross-Coupling Reactions . Vol. 2. de Mejijere A, Diederich F. Wiley-VCH; Weinheim: 2004: 761-814

7a Moerlein SM. J. Org. Chem. 1987; 52: 664
7b Zhang Z, Pitteloud J.-P, Cabrera L, Liang Y, Toribio M, Wnuk SF. Org. Lett. 2010; 12: 816

8a Song RJ, Deng CL, Xie YX, Li JH. Tetrahedron Lett. 2007; 48: 7845
8b Lam PY. S, Deudon S, Averill KM, Li R, He MY, DeShong P, Clark CG. J. Am. Chem. Soc. 2000; 122: 7600

9 Zhang Q, Chen J, Liu M, Wu H, Cheng J, Qin C, Su W, Ding J. Synlett 2008; 935
10 Representative Procedure A Schlenk reaction tube was charged with phenyltrimethylgermane (2a, 194.9 mg, 1.0 mmol), 4-methoxyaniline (1m, 147.9 mg, 1.2 mmol), Pd(OAc)₂ (11.2 mg, 5 mol%), Ph₃P (13.1 mg, 5 mol%), NaOAc (164.1 mg, 2.0 mmol), toluene (2.0 mL), under argon atmosphere at 100 °C for 12 h. After completion of the reaction, as indicated by TLC, the reaction mixture was extracted with Et₂O (3 × 10 mL). The combined organic layer was washed by water and dried by Na₂SO₄. The solvent was removed in vacuo, and the residue was purified by a short column chromatography (silica gel 300–400 mesh, PE–EtOAc = 8:1) to give 3m in 87% isolated yield (173 mg); mp 102–103 °C. 4-Methoxy-N-Phenylaniline (3m) ¹H NMR (300 MHz, CDCl₃): δ = 7.25–7.18 (m, 3 H), 7.09–7.05 (m, 2 H), 6.92–6.83 (m, 4 H), 5.49 (s, 1 H), 3.81 (s, 3 H). ¹³C NMR (75 MHz, CDCl₃): δ = 135.7, 129.3, 124.3, 122.2, 119.5, 115.6, 114.6, 114.1, 55.6. MS (EI): m/z = 212. Anal. Calcd for C₁₃H₁₃NO: C, 78.35; H, 6.59; N, 7.02. Found: C, 78.22; H, 6.41; N, 6.95.

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