Gold-Catalyzed Tandem Reactions of 2-Alkynyl Arylazides: Efficient Access to 3-Alkynyl Indoles

doi:10.6023/cjoc201501045

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (8): 1700-1706.DOI: 10.6023/cjoc201501045 Previous Articles Next Articles

ARTICLE

金催化2-炔基芳基叠氮串联反应有效合成3-炔基吲哚

张小祥, 孙小萍, 崔杏丽, 张海飞

南京林业大学化工学院江苏省生物质绿色燃料与化学品重点实验室南京 210037

收稿日期:2015-01-30 修回日期:2015-03-23 发布日期:2015-03-24
通讯作者: 张小祥 E-mail:s070038@hotmail.com
基金资助:
国家自然科学青年基金(No. 21302096)、江苏省自然科学青年基金(No. BK20130962)和江苏高校优势学科建设工程(PAPD)资助项目.

Gold-Catalyzed Tandem Reactions of 2-Alkynyl Arylazides: Efficient Access to 3-Alkynyl Indoles

Zhang Xiaoxiang, Sun Xiaoping, Cui Xingli, Zhang Haifei

College of Chemical Engineering, Jiangsu Key Laboratory of Biomass-based Green Fuels and Chemicals, Nanjing Forestry University, Nanjing 210037

Received:2015-01-30 Revised:2015-03-23 Published:2015-03-24
Supported by:
Project supported by the Young National Natural Science Foundation of China (No. 21302096), the Young Natural Science Foundation of Jiangsu Province (No. BK20130962) and the Project Fund from the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD).

1. Gold-Catalyzed Tandem Reactions of 2-Alkynyl Arylazides: Efficient Access to 3-Alkynyl Indoles.PDF(6530KB)

Abstract

3-Alkynyl indoles were efficiently prepared through trapping of α-imine gold carbenes by alkynes, generated by gold-catalyzed tandem reactions of 2-alkynyl arylazides. The desired products were afforded up to 94% yield at 60 ℃ with 2 mol% JohnPhosAuCl as catalyst. A very simple and general synthetic method for the efficient synthesis of 3-alkynyl indoles was provided.

Key words: α-imino gold carbene, tandem reaction, alkyne, 3-alkynyl indole

Cite this article

Zhang Xiaoxiang, Sun Xiaoping, Cui Xingli, Zhang Haifei. Gold-Catalyzed Tandem Reactions of 2-Alkynyl Arylazides: Efficient Access to 3-Alkynyl Indoles[J]. Chin. J. Org. Chem., 2015, 35(8): 1700-1706.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Kochanowska-Karamyan, A. J.; Hamann, M. T. Chem. Rev. 2010, 110, 4489. (b) McKay, M. J.; Carroll, A. R.; Quinn, R. J.; Hooper, J. N. A. J. Nat. Prod. 2002, 65, 595.
[2] Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172.
[3] (a) Cacchi, S.; Fabrizi, G. Chem. Rev. 2005, 105, 2873. (b) Seregin, I. V.; Ryabova, V.; Gevorgyan, V. J. Am. Chem. Soc. 2007, 129, 7742. For recent examples of Pd-catalyzed arylation of indoles, see: (c) Lane, B. S.; Sames, D. Org. Lett. 2004, 6, 2897. (d) Lane, B. S.; Brown, M. A.; Sames, D. J. Am. Chem. Soc. 2005, 127, 8050. (e) Bressy, C.; Alberico, D.; Lautens, M. J. Am. Chem. Soc. 2005, 127, 13148. (f) Deprez, N. R.; Kalyani, D.; Krause, A.; Sanford, M. S. J. Am. Chem. Soc. 2006, 128, 4972. (g) Wang, X.; Gribkov, D. V.; Sames, D. J. Org. Chem. 2007, 72, 1476. (h) Dwight, T. A.; Rue, N. R.; Charyk, D.; Josselyn, R.; DeBoef, B. Org. Lett. 2007, 9, 3137. (i) Stuart, D. R.; Villemure, E.; Fagnou, K. J. Am. Chem. Soc. 2007, 129, 12072. For recent examples of Pd-catalyzed vinylation of indoles, see: (j) Jia, C.; Lu, W.; Kitamura, T.; Fujiwara, Y. Org. Lett. 1999, 1, 2097. (k) Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2003, 125, 95783. (l) Liu, C.; Widenhoefer, R. A. J. Am. Chem. Soc. 2004, 126, 10250. (m) Grimster, N. P.; Gauntlett, C.; Godfrey, C. R. A.; Gaunt, M. J. Angew. Chem., Int. Ed. 2005, 44, 3125. (n) Zhang, D.; Qin, Y. Acta Chim. Sinica. 2013, 71, 147 (in Chinese). (张丹, 秦勇, 化学学报, 2013, 71, 147.) (o) Li, S.; Han, J.; Li, A. Acta Chim. Sinica 2013, 71, 295 (in Chinese). (李森, 韩静, 李昂, 化学学报, 2013, 71, 295.) (p) Xie, W.-Q.; Zuo, Z.-W.; Zi, W.-W.; Ma, D.-W. Chin. J. Org. Chem. 2013, 33, 869 (in Chinese). (谢卫青, 左智伟, 资伟伟, 马大为, 有机化学, 2013, 33, 869.) (q) Dan, D.; Jia, Y.-X. Chin. J. Org. Chem. 2013, 33, 1144 (in Chinese). (单冬, 贾彦兴, 有机化学, 2013, 33, 1144.) (r) Liu, Y.-L.; Zhu, F.; Wang, C.-H.; Zhou, J. Chin. J. Org. Chem. 2013, 33, 1595 (in Chinese). (刘运林, 朱锋, 王翠红, 周剑, 有机化学, 2013, 33, 1595.)
[4] (a) Yue, D.; Larock, R. C. Org. Lett. 2004, 6, 1037. (b) Zhang, H.; Larock, R. C. J. Org. Chem. 2002, 67, 7048. (c) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Parisi, L. M. J. Org. Chem. 2005, 70, 6213. (d) Gu, Y.; Wang, X.-M. Tetrahedron Lett. 2009, 50, 763.
[5] For selected reviews on gold catalysis, see: (a) Hashmi, A. S. K. Acc. Chem. Res. 2014, 47, 864. (b) Yeom, H.-S.; Shin, S. Acc. Chem. Res. 2014, 47, 966. (c) Zhang, L. Acc. Chem. Res. 2014, 47, 877. (d) Zhang, S.; Wei, F.; Song, C.; Jia, J.; Xu, Z. Chin. J. Chem. 2014, 32, 937. (e) Gulevich, A. V.; Dudnik, A. S.; Chernyak, N.; Gevorgyan, V. Chem. Rev. 2013, 113, 3084. (f) Zhang, Y.; Luo, S.; Zhu, C. Chin. J. Org. Chem. 2012, 32, 2073 (in Chinese). (张艳, 罗莎, 朱成建, 有机化学, 2012, 32, 2073.) (g) Luo, P.; Tang, R.; Zhong, P.; Li, J. Chin. J. Org. Chem. 2009, 29, 1924 (in Chinese). (罗培松, 汤日元, 钟平, 李金恒, 有机化学, 2009, 29, 1924.) (h) Obradors, C.; Echavarren, A. M. Acc. Chem. Res. 2014, 47, 902. (i) Furstner, A. Chem. Soc. Rev. 2009, 38, 3208. (j) Arcadi, A. Chem. Rev. 2008, 108, 3266. (k) Gorin, D. J.; Sherry, B. D.; Toste, F. D. Chem. Rev. 2008, 108, 3351. (l) Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180. (m) Gorin, D. J.; Toste, F. D. Nature 2007, 446, 395. (n) Li, Z.; Brouwer, C.; He, C. Chem. Rev. 2008, 108, 3239. (o) Gulevich, A. V.; Dudnik, A. S.; Chernyak, N.; Gevorgyan, V. Chem. Rev. 2013, 113, 3084.
[6] (a) Zhang, X.-X.; Sun, X.-P.; Zhang, H.-F.; Cui, X.-L.; Ma, M.-T. Chin. J. Org. Chem. 2015, 35, 1469 (in Chinese). (张小祥, 孙小萍, 张海飞, 崔杏丽, 马猛涛, 有机化学, 2015, 35, 1469.) (b) Gorin, D. J.; Davis, N. R.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 11260. (c) Witham, C. A.; Mauleon, P.; Shapiro, N. D.; Sherry, B. D.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 5838.
[7] (a) Gronnier, C.; Boissonnat, G.; Gagosz, F. Org. Lett. 2013, 15, 4234. (b) Yan, Z.; Xiao, Y.; Zhang, L. Angew. Chem., Int. Ed. 2012, 51, 8624. (c) Xiao, Y.; Zhang, L. Org. Lett. 2012, 14, 4662. (d) Witham, C. A.; Mauleon, P.; Shapiro, N. D.; Sherry, B. D.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 5838. (e) Gorin, D. J.; Davis, N. R.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 11260.
[8] Lu, B.; Luo, Y.; Liu, L.; Ye, L.; Wang, Y.; Zhang, L. Angew. Chem., Int. Ed. 2011, 50, 8358.
[9] Wetzel, A.; Gagosz, F. Angew. Chem., Int. Ed. 2011, 50, 7354.
[10] Li, N.; Wang, T.-Y.; Gong, L.-Z.; Zhang, L. Chem. Eur. J. 2015, 21, 1.
[11] Zhao, L.; Wang, J.; Zhang, H.; Li, Y.; Yang, K.; Cheng, B.; Jin, X.; Yao, Y.; Zhai, H. Org. Lett. 2014, 16, 6378.

[1]	Wenwen Chen, Qin Zhang, Songyue Zhang, Fangfang Huang, Xinyin Zhang, Jianfeng Jia. Visible Light Promoted Coupling Reaction of Alkynyl Iodide and Sodium Sulphinate without Photocatalyst [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 584-592.
[2]	Wenfeng Bei, Jian Pan, Dongmei Ran, Yilin Liu, Zhen Yang, Ruokun Feng. Cobalt-Catalyzed [4+2] Annulation of Indole Carboxamide with Diynes and Monoacetylene: Direct Access to γ-Carbolinones [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3226-3238.
[3]	Changjun Liu, Huiling Hu, Chenghong Liu, Chaojie Zhu, Tiandi Tang. Pd Supported on Mesoporous ETS-10 Zeolite Catalyst with Superior Catalytic Performances in Synthesizing 1,2-Diones from the Oxidation of Internal Alkynes [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2953-2960.
[4]	Suzhen Zhang, Wenwen Zhang, Hui Yang, Qing Gu, Shuli You. Rhodium-Catalyzed Enantioselective Spiroannulation of 2-Alkenylphenols with Alkynes [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2926-2933.
[5]	Kai Lu, Haoqi Qu, Xi Chen, Hui Qiu, Jing Zheng, Mengtao Ma. Catalyst-Free and Solvent-Free Hydroboration of Alkynes and Alkenes with Catecholborane [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2197-2205.
[6]	Jiamin Ma, Jiaoxiong Li, Qiansen Meng, Xianghua Zeng. Advances on the Radical Sulfonation of Alkynes [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2040-2052.
[7]	Sida Li, Xing-Zhong Shu, Lipeng Wu. Zirconium and Titanium Mediated Hydroboration of Alkenes and Alkynes [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1751-1760.
[8]	Zhihao Chen, Qi Fan, Biaolin Yin, Qingjiang Li, Honggen Wang. Progress in the Syntheses of α-Boryl Carbonyl Compounds [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1706-1712.
[9]	Shiquan Gao, Chuangjun Liu, Junfeng Yang, Junliang Zhang. Cobalt-Catalyzed Electrochemical Reductive Coupling of Alkynes and Alkenes [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1559-1565.
[10]	Peng Liu, Fuming Zhong, Lihao Liao, Weiqiang Tan, Xiaodan Zhao. Progress in the Construction of Spirocyclohexadienones via Alkyne-Involving Dearomatization [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4019-4035.
[11]	Chong Tian, Qi Sun, Junfeng Wang, Qiao Chen, Zhiguo Wen, Maxim Borzov, Wanli Nie. E-Stereospecific 1,1-Carboboration of Terminal Arylalkynes with [IB(C₆F₅)₃]^– [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 338-344.
[12]	Qi Sun, Zeying Sun, Ze Yu, Guangwei Wang. Nickel-Catalyzed Stereoselective Aryl-Difluoroalkylation of Alkynes [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2515-2520.
[13]	Fei Chen, Sheng Tao, Ning Liu, Bin Dai. CNN-Type Binuclear Cu(I) Complexes Catalyzed Direct Carboxylation via the Fixation of CO₂ at Room Temperature [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2471-2480.
[14]	Jinsong Hou, Gaosheng Yang. Reaction of Tandem Addition of Aliphatic Amines to Alkenylnitriles Catalyzed by Tris(o-dimethylaminobenzyl)yttrium [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2070-2078.
[15]	Liwen Ma, Xiaoye Wei, Zilin Zhao, Ang Zhao, Xiangwen Deng, Bingnan Huo, Gang Ma, Chunfang Zhang. Theoretical Study on the Catalytic Mechanism of Copper with Various Valence for the Terminal Alkyne Coupling Reaction [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1811-1819.

金催化2-炔基芳基叠氮串联反应有效合成3-炔基吲哚

Gold-Catalyzed Tandem Reactions of 2-Alkynyl Arylazides: Efficient Access to 3-Alkynyl Indoles

PDF

Supporting Info.

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments