Palladium/N-Heterocyclic Carbene Catalyzed Mono- and Double-Cyanation of Aryl Halides Using Potassium Ferrocyanide Trihydrate under Aerobic Conditions

Zhicheng Xu; Yunqing Xiao; Hong Ding; Changsheng Cao; Haitao Li; Guangsheng Pang; Yanhui Shi

doi:10.1055/s-0034-1379899

Synthesis, Table of Contents

Synthesis 2015; 47(11): 1560-1566
DOI: 10.1055/s-0034-1379899

paper

Palladium/N-Heterocyclic Carbene Catalyzed Mono- and Double-Cyanation of Aryl Halides Using Potassium Ferrocyanide Trihydrate under Aerobic Conditions

Authors

Zhicheng Xu

^aSchool of Chemistry and Chemical Engineering and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 221116, P. R. of China
Yunqing Xiao

^aSchool of Chemistry and Chemical Engineering and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 221116, P. R. of China
Hong Ding

^bState Key Laboratory of Inorganic Synthesis and Preparative Chemistry, Jilin University, Changchun, Jilin 130012, P. R. of China Email: yhshi@jsnu.edu.cn
Changsheng Cao*

^aSchool of Chemistry and Chemical Engineering and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 221116, P. R. of China
Haitao Li

^aSchool of Chemistry and Chemical Engineering and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 221116, P. R. of China
Guangsheng Pang

^bState Key Laboratory of Inorganic Synthesis and Preparative Chemistry, Jilin University, Changchun, Jilin 130012, P. R. of China Email: yhshi@jsnu.edu.cn
Yanhui Shi*

^aSchool of Chemistry and Chemical Engineering and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 221116, P. R. of China

Abstract

All articles of this category

Abstract

A practical palladium/N-heterocyclic carbene catalyzed procedure for the mono- and double-cyanation of aryl halides is described using inexpensive, easy-to-handle and nontoxic potassium ferrocyanide trihydrate {K₄[Fe(CN)₆]·3H₂O} as the cyanating agent. The reaction does not require an anhydrous solvent, or the exclusion of air or moisture. A variety of electron-rich and electron-deficient aryl halides are efficiently converted into their corresponding nitriles and dicarbonitriles.

Key words

cyanation - N-heterocyclic carbene - palladium catalysis - potassium ferrocyanide - aerobic conditions

Full Text

References

References

1a Kleeman A, Engel J, Kutscher B, Reichert D. Pharmaceutical Substances: Syntheses, Patents, Applications . 4th ed. Thieme; Stuttgart: 2001
1b Sriram D, Yogeeswari P. Medicinal Chemistry . Pearson Education; Munchen: 2007

2a Larock RC. Comprehensive Organic Transformations: A Guide to Functional Group Preparations. VCH; Weinheim: 1989
2b Rappoport Z. Chemistry of the Cyano Group . Wiley; London: 1970
2c Anbarasan P, Schareina T, Beller M. Chem. Soc. Rev. 2011; 40: 5049

3a Lindley J. Tetrahedron 1984; 40: 1433
3b Bacon RG. R, Hill HA. O. J. Chem. Soc. 1964; 1097
3c Mowry DT. Chem. Rev. 1948; 42: 189

4a Hodgson HH. Chem. Rev. 1947; 40: 251
4b Galli C. Chem. Rev. 1988; 88: 765

5a Stevenson AC. Ind. Eng. Chem. 1949; 41: 1846
5b Denton WI, Bishop RB, Caldwell HP, Chapman HD. Ind. Eng. Chem. 1950; 42: 796
5c Martin A, Wolf GU, Steinike U, Lucke B. J. Chem. Soc., Faraday Trans. 1998; 94: 2227

6a Arvela RK, Leadbeater NE. J. Org. Chem. 2003; 68: 9122
6b Sakakibara Y, Ido Y, Sasaki K, Sakai M, Uchino N. Bull. Chem. Soc. Jpn. 1993; 66: 2776
6c Cassar L, Ferrara S, Foa M. Adv. Chem. Ser. 1974; 132: 252
6d Cassar L, Foa M, Montanari F, Marinelli GP. J. Organomet. Chem. 1979; 173: 335
6e Sakakibara Y, Okuda F, Shimoyabashi A, Kirino K, Sakai M, Uchino N, Takagi K. Bull. Chem. Soc. Jpn. 1988; 61: 1985
6f Takagi K, Sakakibara Y. Chem. Lett. 1989; 1957

7a Cristau H.-J, Ouali A, Spindler J.-F, Taillefer M. Chem. Eur. J. 2005; 11: 2483
7b Zanon J, Klapars A, Buchwald SL. J. Am. Chem. Soc. 2003; 125: 2890
7c Wu JX, Beck B, Ren RX. Tetrahedron Lett. 2002; 43: 387
7d Schareina T, Zapf A, Magerlein W, Muller N, Beller M. Chem. Eur. J. 2007; 13: 6249
7e Schareina T, Zapf A, Beller M. Tetrahedron Lett. 2005; 46: 2585
7f Schareina T, Zapf A, Cotte A, Gotta M, Beller M. Adv. Synth. Catal. 2011; 353: 777
7g Ren Y, Wang W, Zhao S, Tian X, Wang J, Yin W, Cheng L. Tetrahedron Lett. 2009; 50: 4595
7h Giachi G, Frediani M, Oberhauser W, Lamaty F, Martinez J, Colacino E. ChemSusChem 2014; 7: 919

8a Anderson BA, Bell EC, Ginah FO, Harn NK, Pagh LM, Wepsiec JP. J. Org. Chem. 1998; 63: 8224
8b Maligres PE, Waters MS, Fleitz F, Askin D. Tetrahedron Lett. 1999; 40: 8193
8c Jin F, Confalone PN. Tetrahedron Lett. 2000; 41: 3271
8d Sundermeier M, Zapf A, Mutyala S, Baumann W, Sans J, Weiss S, Beller M. Chem. Eur. J. 2003; 9: 1828
8e Chidambaram R. Tetrahedron Lett. 2004; 45: 1441
8f Yang C, Williams JM. Org. Lett. 2004; 6: 2837
8g Schareina T, Zapf A, Beller M. Chem. Commun. 2004; 1388
8h Schareina T, Zapf A, Beller M. J. Organomet. Chem. 2004; 689: 4576
8i Stazi F, Palmisano G, Turconi M, Santagostino M. Tetrahedron Lett. 2005; 46: 1815
8j Jensen RS, Gajare AS, Toyota K, Yoshifuji M, Ozawa F. Tetrahedron Lett. 2005; 46: 8645
8k Hatsuda M, Seki M. Tetrahedron 2005; 61: 9908
8l Weissman SA, Zewge D, Chen C. J. Org. Chem. 2005; 70: 1508
8m Grossman O, Gelman D. Org. Lett. 2006; 8: 1189
8n Pitts MR, McCormack P, Whittall J. Tetrahedron 2006; 62: 4705
8o Littke A, Soumeillant M, Kaltenback III RF, Cherney RJ, Tarby CM, Kiau S. Org. Lett. 2007; 9: 1711
8p Schareina T, Zapf A, Magerlein W, Muller N, Beller M. Tetrahedron Lett. 2007; 48: 1087
8q Shevlin M. Tetrahedron Lett. 2010; 51: 4833
8r Gerber R, Oberholzer M, Frech CM. Chem. Eur. J. 2012; 18: 2978
8s Ushkov AV, Grushin VV. J. Am. Chem. Soc. 2011; 133: 10999
8t Zhang J, Chen X, Hu T, Zhang Y, Xu K, Yu Y, Huang J. Catal. Lett. 2010; 139: 56
8u Chatterjee T, Dey R, Ranu BC. J. Org. Chem. 2014; 79: 5875
8v Takagi K, Okamoto T, Sakakibara Y, Oka S. Chem. Lett. 1973; 471

9a Fortman GC, Nolan SP. Chem. Soc. Rev. 2011; 40: 5151
9b Diez-Gonzalez S, Marion N, Nolan SP. Chem. Rev. 2009; 109: 3612
9c Arnold PL, Casely IJ. Chem. Rev. 2009; 109: 3599
9d Enders D, Niemeier O, Henseler A. Chem. Rev. 2007; 107: 5606
9e Dröge T, Glorius F. Angew. Chem. Int. Ed. 2010; 49: 6940
9f Bugaut X, Glorius F. Chem. Soc. Rev. 2012; 41: 3511
9g Moore JL, Rovis T. Top. Curr. Chem. 2010; 291: 77

10a Cao C, Wang L, Cai Z, Zhang L, Guo J, Pang G, Shi Y. Eur. J. Org. Chem. 2011; 8: 1570
10b Yang L, Guan P, He P, Chen Q, Cao C, Peng Y, Shi Z, Pang G, Shi Y. Dalton Trans. 2012; 41: 5020
10c Yang L, Li Y, Chen Q, Du Y, Cao C, Pang G, Shi Y. Tetrahedron 2013; 69: 5178
10d Li Y, Liu G, Cao C, Wang S, Li Y, Pang G, Shi Y. Tetrahedron 2013; 69: 6241
10e Chen Q, Lv L, Yu M, Shi Y, Li Y, Pang G, Cao C. RSC Adv. 2013; 3: 18359
10f He P, Du Y, Liu G, Cao C, Shi Y, Zhang J, Pang G. RSC Adv. 2013; 3: 18345

Supplementary Material

Supporting Information (PDF) (opens in new window)