Copper-Catalyzed Cyanation of Arylboronic Acids Using DDQ as Cyanide Source

Guangyou Zhang; Shuyou Chen; Haiyang Fei; Jiang Cheng; Fan Chen

doi:10.1055/s-0031-1290451

Synlett, Inhaltsverzeichnis

Synlett 2012; 23(15): 2247-2250
DOI: 10.1055/s-0031-1290451

letter

Copper-Catalyzed Cyanation of Arylboronic Acids Using DDQ as Cyanide Source

Authors

Guangyou Zhang

^aCollege of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325000, P. R. of China, eMail: fanchen@wzu.edu.cn
Shuyou Chen

^aCollege of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325000, P. R. of China, eMail: fanchen@wzu.edu.cn
Haiyang Fei

^bSchool of Petrochemical Engineering, Changzhou University, Changzhou 213164, P. R. of China, Fax: +86(577)56998939 eMail: jiangcheng@cczu.edu.cn
Jiang Cheng*

^bSchool of Petrochemical Engineering, Changzhou University, Changzhou 213164, P. R. of China, Fax: +86(577)56998939 eMail: jiangcheng@cczu.edu.cn
Fan Chen*

^aCollege of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325000, P. R. of China, eMail: fanchen@wzu.edu.cn

Abstract

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Abstract

In this paper, a copper-catalyzed cyanation of arylboronic acids is achieved with DDQ, providing nitriles with good yields. This new approach represents a safe method for the synthesis of aryl nitriles.

Key words

copper - cyanation - arylboronic acids - nitriles - DDQ

Volltext

Referenzen

References and Notes

1a Kleemann A, Engel J, Kutscher B, Reichert D. Pharmaceutical Substances: Syntheses, Patents, Applications . 4th ed.. Thieme; Stuttgart: 2001
1b Nagamura S, Kobayashi E, Gomi K, Saito H. Bioorg. Med. Chem. 1996; 4: 1379
1c Njar VC. O, Brodie AM. H. Drugs 1999; 58: 233

2a Rappoport Z. The Chemistry of the Cyano Group . Interscience; New York: 1970
2b Larock RC. Comprehensive Organic Transformations . Wiley-VCH; New York: 1988

3a Sandmeyer T. Ber. Dtsch. Chem. Ges. 1884; 17: 1633
3b Hodgson HH. Chem. Rev. 1947; 40: 251
3c Ellis GP, Romney-Alexander TM. Chem. Rev. 1987; 87: 779
3d Lindley J. Tetrahedron 1984; 40: 1433

4a Anbarasan P, Schareina T, Beller M. Chem. Soc. Rev. 2011; 40: 5049
4b Yeung PY, So CM, Lau CP, Kwong FY. Angew. Chem. Int. Ed. 2010; 49: 8918
4c Chen J, Sun Y, Liu B, Liu D, Cheng J. Chem. Commun. 2012; 48: 449
4d Zhang D, Sun H, Zhang L, Zhou Y, Li C, Jiang H, Chen K, Liu H. Chem. Commun. 2012; 48: 2909
4e Yeung PY, Tsang CP, Kwong FY. Tetrahedron Lett. 2011; 52: 7038
4f Zhou W, Chen W, Wang L. Org. Biomol. Chem. 2012; 10: 4172

5a Do H.-Q, Daugulis O. Org. Lett. 2010; 12: 2517
5b Qin C, Jiao N. J. Am. Chem. Soc. 2010; 132: 15893
5c Mariampillai B, Alliot J, Li M, Lautens M. J. Am. Chem. Soc. 2007; 129: 15372
5d Yan G, Kuang C, Zhang Y, Wang J. Org. Lett. 2010; 12: 1052
5e Lu Z, Hu C, Guo J, Li J, Cui Y, Jia Y. Org. Lett. 2010; 12: 480
5f Zhou W, Xu J, Zhang L, Jiao N. Org. Lett. 2010; 12: 2888
5g Zhang G, Lv G, Pan C, Cheng J, Chen F. Synlett 2011; 2991
5h Subba Reddy B, Begum VZ, Jayasudhan Reddy YJ. Tetrahedron Lett. 2010; 51: 3334
5i Mariampillai B, Alberico D, Bidau V, Lautens M. J. Am. Chem. Soc. 2006; 128: 14436
5j Dohi T, Morimoto K, Kiyono Y, Tohma H, Kita Y. Org. Lett. 2005; 7: 537
5k Chen X, Hao X.-S, Goodhue CE, Yu J.-Q. J. Am. Chem. Soc. 2006; 128: 6790
5l Okamoto K, Watanabe M, Murai M, Hatano R, Ohe K. Chem. Commun. 2012; 48: 3127
5m Jia X, Yang D, Wang W, Luo F, Cheng J. J. Org. Chem. 2009; 74: 9470
5n Jia X, Yang D, Zhang S, Cheng J. Org. Lett. 2009; 11: 4716
5o Zhang Y, Peng H, Zhan M, Cheng Y, Zhu C. Chem. Commun. 2011; 47: 2354
5p Ushijima S, Moriyama K, Togo H. Tetrahedron 2012; 68: 4588

6 Kim J, Chang S. J. Am. Chem. Soc. 2010; 132: 10272

7a Ren X, Chen J, Chen F, Cheng J. Chem. Commun. 2011; 47: 6725
7b Ding S, Jiao N. J. Am. Chem. Soc. 2011; 133: 12374

8a Zhang G, Ren X, Chen J, Hu M, Cheng J. Org. Lett. 2011; 13: 5004
8b Ushijima S, Togo H. Synlett 2010; 1562
8c Ishii G, Moriyama K, Togo H. Tetrahedron Lett. 2011; 52: 2404
8d Ushijima S, Moriyama K, Togo H. Tetrahedron 2011; 67: 958

9a Sundermeier M, Zapf A, Beller M. Angew. Chem. Int. Ed. 2003; 42: 1661
9b Schareina T, Zapf A, Cotté A, Gotta M, Beller M. Adv. Synth. Catal. 2011; 353: 777
9c Park EJ, Lee S, Chang S. J. Org. Chem. 2010; 75: 2760

10a Anbarasan P, Neumann H, Beller M. Chem.–Eur. J. 2011; 17: 4217
10b Yang Y, Zhang Y, Wang J. Org. Lett. 2011; 13: 5608

11a Thiele J, Günther F. Justus Liebigs Ann. Chem. 1906; 349: 45
11b Walker D, Hiebert JD. Chem. Rev. 1967; 67: 153

12 Zhang Z, Liebeskind LS. Org. Lett. 2006; 8: 4331
13 Liskey CW, Liao X, Hartwig JF. J. Am. Chem. Soc. 2010; 132: 11389
14 Anbarasan P, Neumann H, Beller M. Angew. Chem. Int. Ed. 2011; 50: 519
15 Zhang G, Zhang L, Hu M, Cheng J. Adv. Synth. Catal. 2011; 353: 291
16 Kim J, Choi J, Shin K, Chang S. J. Am. Chem. Soc. 2012; 134: 2528
17 General Procedure of Cyanation Protocol of Arylboronic Acids with DDQ Under air, a reaction tube was charged with arylboronic acids (0.2 mmol), DDQ (45.2 mg, 0.2 mmol), Cu(OTf)₂ (7.2 mg, 10 mol%), K₂CO₃ (41.4 mg, 0.3 mmol), Ag₂CO₃ (55 mg, 0.2 mmol), and dry DMF (2 mL). The mixture was stirred at 100 °C for 20 h. After the completion of the reaction, monitored by TLC, the solvent was evaporated under reduced pressure, and the residue was purified by flash column chromatography on silica gel to give the product. 4-(Methylthio)benzonitrile (3ac) Yellowlish solid; mp 61–62 °C. ¹H NMR (300 MHz, CDCl₃): δ = 7.53 (d, J = 8.7 Hz, 2 H), 7.26 (d, J = 8.7 Hz, 2 H), 2.51 (s, 3 H). ¹³C NMR (125 MHz, CDCl₃): δ = 146.1, 132.2, 125.6, 119.0, 107.7, 14.7. IR (neat): ν = 2223, 1699, 1593, 1483, 1434, 1361, 1218, 1089, 816 cm^–1. HRMS (EI): m/z calcd for C₈H₇NS [M⁺]: 149.0299; found: 149.0291. Methyl 4-Cyanobenzoate (3al) Yellowlish solid; mp 67–68 °C. ¹H NMR (300 MHz, CDCl₃): δ = 8.12 (d, J = 8.1 Hz, 2 H), 7.73 (d, J = 8.1 Hz, 2 H), 3.95 (s, 3 H). ¹³C NMR (125 MHz, CDCl₃): δ = 165.4, 133.9, 132.2, 130.0, 117.9, 116.4, 52.6. IR (neat): ν = 2221, 1699, 1582, 1424, 1358, 1210, 1089 cm^–1. HRMS (EI): m/z calcd for C₉H₇NO₂ [M⁺]: 161.0477; found: 161.0486.

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