Cu-Catalyzed Cyanation of Aryl Iodides with Acetonitrile as Cyano Source

doi:10.6023/cjoc201612015

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (5): 1273-1277.DOI: 10.6023/cjoc201612015 Previous Articles Next Articles

Articles

铜催化的乙腈为氰源的芳基碘化物的氰化（英文）

俞峥炜, 李林奕, 沈增明

上海交通大学化学化工学院上海 200240

收稿日期:2016-12-06 修回日期:2017-01-05 发布日期:2017-01-17
通讯作者: 沈增明 E-mail:shenzengming@sjtu.edu.cn
基金资助:
国家自然科学基金（Nos.21272001，21672144）及上海教育委员会（No.13ZZ014）资助项目.

Cu-Catalyzed Cyanation of Aryl Iodides with Acetonitrile as Cyano Source

Yu Zhengwei, Li Linyi, Shen Zengming

School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240

Received:2016-12-06 Revised:2017-01-05 Published:2017-01-17
Contact: 10.6023/cjoc201612015 E-mail:shenzengming@sjtu.edu.cn
Supported by:
Project supported by the National Natural Sciences Foundation of China (Nos. 21272001, 21672144) and the Shanghai Education Committee (No. 13ZZ014).

1. Cu-Catalyzed Cyanation of Aryl Iodides with Acetonitrile as Cyano Source.PDF(678KB)

Abstract

A Cu-catalyzed protocol for the cyanation of aryl iodides by using acetonitrile as the “CN” source has been developed, in which the Cu(cat.)/2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO)/Si system shows good reactivity and generality. Both electron-rich and electron-deficient functional groups can be tolerated in this system.

Key words: Cu catalyst, cyanation, acetonitrile, aryl iodide, 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO)

Cite this article

Yu Zhengwei, Li Linyi, Shen Zengming. Cu-Catalyzed Cyanation of Aryl Iodides with Acetonitrile as Cyano Source[J]. Chin. J. Org. Chem., 2017, 37(5): 1273-1277.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Kleemann, A.; Engel, J.; Kutschner, B.; Reichert, D. Pharmaceutical Substances: Syntheses, Patents, Applications, 4th ed., Thieme, Stuttgart, New York, 2001, pp. 154, 159, 241, 488, 553, 825.
(b) Miller, J. S.; Manson, J. L. Acc. Chem. Res. 2001, 34, 563.
(c) Fleming, F. F.; Wang, Q. Chem. Rev. 2003, 103, 2035.
[2] (a) Rappoport, Z. The Chemistry of the Cyano Group, Interscience, London, 1970.
(b) Larock, R. C. Comprehensive Organic Transformations: A Guide to Functional Group Preparations, Wiley-VCH, New York, 1989.
[3] For reviews, see: (a) Ellis, G. P.; Romney-Alexander, T. M. Chem. Rev. 1987, 87, 779.
(b) Anbarasan, P.; Schareina, T.; Beller, M. Chem. Soc. Rev. 2011, 40, 5049.
(c) Wen, Q.; Jin, J.; Zhang, L.; Luo, Y.; Lu, P.; Wang, Y. Tetrahedron Lett. 2014, 55, 1271.
(d) Yan, G.; Yu, J.; Zhang, L. Chin. J. Org. Chem. 2012, 32, 294 (in Chinese). (严国兵, 于健, 张玲, 有机化学, 2012, 32, 294.)
(e) Kim, J.; Kim, H.; Chang, S. Angew. Chem., Int. Ed. 2012, 51, 11948.
(f) Ping, Y.; Ding, Q.; Peng, Y. ACS Catal. 2016, 6, 5989.
[4] For some representative examples with KCN, see: (a) Sakakibara, Y.; Okuda, F.; Shimobayashi, A.; Kirino, K.; Sakai, M.; Uchino, N.; Takagi, K. Bull. Chem. Soc. Jpn. 1988, 61, 1985.
(b) Anderson, B. A.; Bell, E.; Ginah, F., O.; Harn, N, K..; Pagh, L.; Wepsiec, J. J. Org. Chem. 1998, 63, 8224.
(c) Cristau, H.; Ouali, A.; Spindler, J.; Taillefer, M. Chem. Eur. J. 2005, 11, 2483.
(d) Yang, C.; Williams, J. M. Org. Lett. 2004, 6, 2837.
(e) Li, C.; Ju, Y.; Liu, F. Org. Lett. 2009, 11, 3582.
(f) Arai, S.; Sato, T.; Nishida, A. Adv. Synth. Catal. 2009, 351, 1897.
(g) Yang, C.; Williams, J. M. Org. Lett. 2004, 6, 2837.
(h) Coughlin, M. M.; Kelly, C.-K.; Lin, S.; MacArthur, M. Organometallics 2013, 32, 3537.
[5] For some representative examples with NaCN, see: (a) Okano, T.; Iwahara, M.; Kiji, J. Synlett 1998, 243.
(b) Zanon, J.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 2890.
(c) Zhang, Z.; Wang, Z.; Zhang, R.; Ding, K. Angew. Chem., Int. Ed. 2010, 49, 6746.
(d) Do, H. Q.; Daugulis, O. Org. Lett. 2010, 12, 2517.
(e) Murahashi, S. I.; Nakae, T.; Terai, H.; Komiya, N. J. Am. Chem. Soc. 2008, 130, 11005.
(f) Erhardt, S.; Grushin, V. V.; Kilpatrick, A. H.; Macgregor, S. A.; Marshall, W. J.; Roe, D. C. J. Am. Chem. Soc. 2008, 130, 4828.
(g) Ushkov, A. V.; Grushin, V. V. J. Am. Chem. Soc. 2011, 133, 10999.
(h) Cristau, H. J.; Ouali, A.; Spindler, J. F.; Taillefer, M. Chem.-Eur. J. 2005, 11, 2483.
[6] For some representative examples with TMSCN, see: (a) Arai, S.; Koike, Y.; Nishida, A. Adv. Synth. Catal. 2010, 352, 893.
(b) Arai, S.; Sato, T.; Koike, Y.; Hayashi, M.; Nishida, A. Angew. Chem., Int. Ed. 2009, 48, 4528.
(c) Han, W.; Ofial, A. R. Chem. Commun. 2009, 5024.
(d) Chen, G.; Wang, Z.; Wu, J.; Ding, K. Org. Lett. 2008, 10, 4573.
(e) Zhang, W.; Wang, F.; McCann, S. D.; Wang, D.; Chen, P.; Stahl, S. S.; Liu, G. Science 2016, 353, 1014.
(f) Ye, X.; Zeng, X.; Zhou, J. Acta Chim. Sinica 2016, 74, 984 (in Chinese). (叶旭, 曾兴平, 周剑, 化学学报, 2016, 74, 984.)
[7] For some representative examples with K₄[Fe(CN)₆], see: (a) Schareina, T.; Zapfa, A.; Beller, M. Chem. Commun. 2004, 1388.
(b) Weissman, S. A.; Zewge, D.; Chen, C. J. Org. Chem. 2005, 70, 1508.
(c) Schareina, T.; Zapf, A.; Beller, M. Tetrahedron Lett. 2005, 46, 2585.
(d) Grossman, O.; Gelman, D. Org. Lett. 2006, 8, 1189.
(e) Schareina, T.; Zapf, A.; Mägerlein, W.; Müller, N.; Beller, M.; Tetrahedron Lett. 2007, 48, 1087.
(f) Anbarasan, P.; Schareina, T.; Beller, M. Chem. Soc. Rev. 2011, 40, 5049.
(g) Yeung, P. Y.; So, C. M.; Lau, C. P.; Kwong, F. Y. Angew. Chem., Int. Ed. 2010, 49, 8918.
[8] For some representative examples with BnCN, see: (a) Wen, Q.; Jin, J.; Hu, B.; Lu, P.; Wang, Y. RSC Adv. 2012, 2, 6167.
(b) Jin, J.; Wen, Q.; Lu, P.; Wang, Y. Chem. Commun. 2012, 48, 9933.
(c) Zhang, L.; Wen, Q.; Jin, J.; Wang, C.; Lu, P.; Wang, Y. Tetrahedron 2013, 69, 4236.
(d) Luo, Y.; Wen, Q.; Wu, Z.; Jin, J.; Lu, P.; Wang, Y. Tetrahedron 2013, 69, 8400.
[9] For some representative examples with t-BuNC, see: (a) Xu, S.; Huang, X.; Hong, X.; Xu, B. Org. Lett. 2012, 14, 4614.
(b) Peng, J.; Zhao, J.; Hu, Z.; Liang, D.; Huang, J.; Zhu, Q. Org. Lett. 2012, 14, 4966.
(c) Hong, X.; Wang, H.; Qian, G.; Tan, Q.; Xu, B. J. Org. Chem. 2014, 79, 3228.
[10] Whitten, J. P.; McCarthy, J. R.; Matthews, D. P. Synthesis 1988, 470.
[11] (a) Kim, J.; Choi, J.; Shin, K.; Chang, S. J. Am. Chem. Soc. 2012, 134, 2528.
(b) Kim, J.; Kim, H.; Chang, S. Org. Lett. 2012, 14, 3924.
(c) Wang, Z.; Chang, S. Org. Lett. 2013, 15, 1990.
[12] Zhang, G.; Ren, X.; Chen, J.; Hu, M.; Cheng, J. Org. Lett. 2011, 13, 5004.
[13] (a) Ren, X.; Chen, J.; Chen, F.; Cheng, J. Chem. Commun. 2011, 47, 6725.
(b) Kishore, R.; Yadav, J.; Venu, B.; Venugopala, A.; Kantam, M. L. New J. Chem. 2015, 39, 5259.
[14] (a) Song, R.-J.; Wu, J.-C.; Liu, Y.; Deng, G.-B.; Wu, C.-Y.; Wei, W.-T.; Li, J.-H. Synlett 2012, 2491.
(b) Pan, C.; Jin, H.; Xu, P.; Liu, X.; Cheng, Y.; Zhu, C. J. Org. Chem. 2013, 78, 9494
(c) Xu, W.; Xu, Q.; Li, J. Org. Chem. Front. 2015, 2, 231.
(d) Luo, F.-H.; Chu, C.-I.; Cheng, C.-H. Organometallics 1998, 17, 1025.
(e) Hu, W.; Teng, F.; Peng, H.; Yu, J.; Sun, S.; Cheng, J.; Shao, Y. Tetrahedron Lett. 2015, 56, 7056.
[15] (a) Kou, X.; Zhao, M.; Qiao, X.; Zhu, Y.; Tong, X.; Shen, Z. Chem. Eur. J. 2013, 19, 16880.
(b) Zhu, Y.; Li, L.; Shen, Z. Chem. Eur. J. 2015, 21, 13246.
(c) Zhu, Y.; Zhao, M.; Lu, W.; Li, L.; Shen, Z. Org. Lett. 2015, 17, 2602.
(d) Zhao, M.; Zhang, W.; Shen, Z. J. Org. Chem. 2015, 80, 8868.
[16] Pawar, A. B.; Chang, S. Chem. Commun. 2014, 50, 448.
[17] (a) Zheng, K.; Yu, P.; Chen, S.; Chen, F.; Cheng, J. Chin. J. Chem. 2013, 31, 449.
(b) Wang, L.; Pan, L.; Chen, C.; He, M. Chin. J. Chem. 2014, 32, 1221.

铜催化的乙腈为氰源的芳基碘化物的氰化（英文）

Cu-Catalyzed Cyanation of Aryl Iodides with Acetonitrile as Cyano Source

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Yang Li, Yanan Dong, Yuehui Li. Efficient Synthesis of Nitrile Compounds through Amide Conversion via N-Boroamide Intermediates [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 638-643.
[2]	Yuanlin Cai, Ya Lü, Guihua Nie, Zhichao Jin, Yonggui Chi. Recent Advances in the Synthesis of Cyanides Enabled by N-Heterocyclic Carbene Catalysis [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3135-3145.
[3]	Hu Ma, Danfeng Huang, Kehu Wang, Duoduo Tang, Yang Feng, Yuanyuan Reng, Junjiao Wang, Yulai Hu. Synthesis of 3-Trifluoromethylpyrazole Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3257-3267.
[4]	Zhongrong Xu, Jieping Wan, Yunyun Liu. Transition Metal-Free C—H Thiocyanation and Selenocyanation Based on Thermochemical, Photocatalytic and Electrochemical Process [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2425-2446.
[5]	Chuanchuan Wang, Zhiwei Ma, Xuehui Hou, Longhua Yang, Yajing Chen. Research and Application of N-Ts Cyanamides in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 74-93.
[6]	Yu Zheng, Shencheng Qian, Pengcheng Xu, Binnan Zheng, Shenlin Huang. Electrochemical Oxidative Thiocyanosulfonylation of Aryl Acetylenes [J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4275-4281.
[7]	Yunshu Liu, Guodong Zhao, Wenju Wu, Yunze Wang, Yanchao Yu, Jun You, Bo Liu. Study on Asymmetric Conjugate Cyanation of 3,5-Dimethyl-N-α,β-unsaturated Acylpyrazole Catalyzed by Magnesium-Bisoxazoline Complex [J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 208-217.
[8]	Tao Zhang, Shangda Li, Chunlin Zhou, Xinchao Wang, Meng Zhang, Zezhong Gao, Gang Li. Site-Selective C—H Iodination of Phenol Derivatives Using Aryl Iodide as Iodinating Reagent [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3511-3520.
[9]	Junqing Gao, Xinjun Weng, Cong Ma, Xuetao Xu, Ping Fang, Tiansheng Mei. Electrochemical 2,2,6,6-tetramethylpiperidinyl-N-oxyl (TEMPO)-Mediated α-Cyanation and Phosphonylation of Cyclic Amines with Metal-Free Conditions [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3223-3234.
[10]	Wu Yan, Tian Xianzhi, Zhang Hailing, Chen Rui, Cao Tuanwu. Microwave-Assisted Iodine-Catalyzed 3-Selenocyanation of Indole for the Synthesis of 3-Selenocyanateindole Derivatives [J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1384-1387.
[11]	Zhang Longfei, Niu Cong, Yang Xiaoting, Qin Hongyun, Yang Jianjing, Wen Jiangwei, Wang Hua. Recent Advances on the Photocatalytic and Electrocatalytic Thiocyanation Reactions [J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1117-1128.
[12]	Xu Weigang, Huang Danfeng, Wang Kehu, Zhao Fangxia, Zhao Zhuanxia, Hu Yongqing, Su Yingpeng, Hu Yulai. Study on the Hydrocyanation Reaction of Trifluoromethylated Acylhydrazones [J]. Chinese Journal of Organic Chemistry, 2020, 40(4): 922-929.
[13]	Qian Cunwei, Zhu Wenqian, Liu Junlong, Wang Xuemin, Qiu Ligan. Chitosan@Cu₂O as A Facile, Efficient and Reusable Catalyst for Ligand-Free C-O and C-N Coupling [J]. Chin. J. Org. Chem., 2019, 39(6): 1695-1703.
[14]	Ahmad Muhammad Siddique, Zhu Yamin, Guo Yunlong, Zhang Saisai, Shen Zengming. Copper-Catalyzed Aerobic Oxidation Strategy: A Concise Route to Isatin [J]. Chinese Journal of Organic Chemistry, 2019, 39(11): 3244-3249.
[15]	Qi Haitang, Song Guanglin, Quan Zhengjun, Wang Xicun. CuSO₄·5H₂O/NaAsc-Catalyzed Sonogashira Coupling Reaction of Aryl Iodides and Terminal Alkynes [J]. Chin. J. Org. Chem., 2017, 37(7): 1855-1859.