Gold-Catalyzed Tandem Reactions of 2-Alkynyl Arylazides and Carboxylic Acids for the Synthesis of 1H-Indol-3-yl Esters

doi:10.6023/cjoc201501020

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (7): 1469-1474.DOI: 10.6023/cjoc201501020 Previous Articles Next Articles

Articles

金催化2-炔基芳基叠氮与羧酸串联反应合成3-吲哚酯

张小祥^a, 孙小萍^a, 张海飞^a, 崔杏丽^a, 马猛涛^b

a 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;
b 南京林业大学理学院南京 210037

收稿日期:2015-01-15 修回日期:2015-03-17 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)、江苏高校优势学科建设工程(PAPD)和国家自然科学基金(No. 21372117)资助项目.

Gold-Catalyzed Tandem Reactions of 2-Alkynyl Arylazides and Carboxylic Acids for the Synthesis of 1H-Indol-3-yl Esters

Zhang Xiaoxiang^a, Sun Xiaoping^a, Zhang Haifei^a, Cui Xingli^a, Ma Mengtao^b

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

Received:2015-01-15 Revised:2015-03-17 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), the Project Fund from the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD) and the National Natural Science Foundation of China (No. 21372117).

1. Gold-Catalyzed Tandem Reactions of 2-Alkynyl Arylazides and Carboxylic Acids for the Synthesis of 1H-Indol-3-yl Esters.PDF(4841KB)

Abstract

1H-Indol-3-yl acetates are very important indole derivatives, which can be found in many bioactive compounds and natural products. In this work, 1H-indol-3-yl acetates were efficiently prepared via α-imino gold carbenes generated by gold-catalyzed reactions of 2-alkynyl arylazides. A very simple and general method for the synthesis of 1H-indol-3-yl acetates was provided after examining the substrates scope.

Key words: 2-alkynyl arylazides, tandem reactions, carboxylic acids, 1H-indol-3-yl esters

Cite this article

Zhang Xiaoxiang, Sun Xiaoping, Zhang Haifei, Cui Xingli, Ma Mengtao. Gold-Catalyzed Tandem Reactions of 2-Alkynyl Arylazides and Carboxylic Acids for the Synthesis of 1H-Indol-3-yl Esters[J]. Chin. J. Org. Chem., 2015, 35(7): 1469-1474.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Bandini, M.; Eichholzer, A. Angew. Chem., Int. Ed. 2009, 48, 9608. (b) Joucla, L.; Djakovitch, L. Adv. Synth. Catal. 2009, 351, 673. (c) Hong, J.; Xun, L.; Hong, W.; Huashan, Z.; Jieke, C. J. Wuhan Univ. (Nat. Sci. Ed.) 1998, 44, 175.
[2] Arnold, R. D.; Nutter, W. M.; Stepp, W. L. J. Org. Chem. 1959, 24, 117.
[3] Liu, K.; Wen, P.; Liu, J.; Huang, G. Synthesis 2010, 3623.
[4] 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) Yan, D.; Wu, C.; Yi, W.-G. Chin. J. Org. Chem. 2014, 34, 1857 (in Chinese). (鄢东, 吴超, 易卫国, 有机化学, 2014, 34, 1857.) (f) Wang, X.-Y.; Li, Z.-Z. Chin. J. Org. Chem. 2014, 34, 566 (in Chinese.) (王小勇, 李治章, 有机化学, 2014, 34, 566.) (g) Gulevich, A. V.; Dudnik, A. S.; Chernyak, N.; Gevorgyan, V. Chem. Rev. 2013, 113, 3084. (h) Zhang, Y.; Luo, S.; Zhu, C.-J. Chin. J. Org. Chem. 2012, 32, 2073 (in Chinese). (张艳, 罗莎, 朱成建, 有机化学, 2012, 32, 2073.) (i) Luo, P.-S.; Tang, R.-Y.; Zhong, P.; Li, J.-H. 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.) (j) Obradors, C.; Echavarren, A. M. Acc. Chem. Res. 2014, 47, 902. (k) Furstner, A. Chem. Soc. Rev. 2009, 38, 3208. (l) Arcadi, A. Chem. Rev. 2008, 108, 3266. (m) Gorin, D. J.; Sherry, B. D.; Toste, F. D. Chem. Rev. 2008, 108, 3351. (n) Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180. (o) Gorin, D. J.; Toste, F. D. Nature 2007, 446, 395. (p) Li, Z.; Brouwer, C.; He, C. Chem. Rev. 2008, 108, 3239. (q) Gulevich, A. V.; Dudnik, A. S.; Chernyak, N.; Gevorgyan, V. Chem. Rev. 2013, 113, 3084.
[5] (a) Li, N.; Wang, T.-Y.; Gong, L.-Z.; Zhang, L. Chem. Eur. J. 2015, 21, 1. (b) Gronnier, C.; Boissonnat, G.; Gagosz, F. Org. Lett. 2013, 15, 4234. (c) Yan, Z.; Xiao, Y.; Zhang, L. Angew. Chem., Int. Ed. 2012, 51, 8624. (d) Xiao, Y.; Zhang, L. Org. Lett. 2012, 14, 4662. (e) Witham, C. A.; Mauleon, P.; Shapiro, N. D.; Sherry, B. D.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 5838. (f) Gorin, D. J.; Davis, N. R.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 11260.
[6] Lu, B.; Luo, Y.; Liu, L.; Ye, L.; Wang, Y.; Zhang, L. Angew. Chem., Int. Ed. 2011, 50, 8358.
[7] Wetzel, A.; Gagosz, F. Angew. Chem., Int. Ed. 2011, 50, 7354.

[1]	Suyan Tao, Zixin Xiang, Junjie Bai, Xiao Wan, Xiaobing Wan. Amide Hydrolysis Reaction Using tert-Butyl Nitrite [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 550-560.
[2]	Chaoyu Wang, Shuda Dong, Tianyang Zhu, Yuqin Liu, Zihan Wu, Ruokun Feng. Cobalt-Catalyzed Decarbonylative C(8)-Acyloxylation of 1-Naphthalamine Derivatives with α-Oxocarboxylic Acids [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1799-1810.
[3]	Yan Zhaohua, Wang Yanmei, Jin Hong'ai, Ai Chengmei, Tian Weisheng. One-Step Enol Esterification of 1,3-Dicarbonyls with Carboxylic Acids Activated by Perfluoroalkanosulfonyl Fluoride [J]. Chin. J. Org. Chem., 2019, 39(7): 2042-2047.
[4]	Tan Jiaxi, Guo Ye, Zeng Fei, Chen Guanrong, Xie Longyong, He Weimin. Synthesis of Sterically Hindered and Electron-Deficient Secondary Amides from Unactivated Carboxylic Acids and Isothiocyanates [J]. Chin. J. Org. Chem., 2018, 38(7): 1740-1748.
[5]	Zhang Xiaoxiang, Lü Chang, Li Ping, Yong Wanxiong, Li Jing, Zhu Xinbao. Rapid Access to 4H-3, 1-Benzoxazin-4-ones via Gold-Catalyzed One-Pot Oxidative Rearrangement of 2-Alkynyl Arylazides [J]. Chin. J. Org. Chem., 2018, 38(1): 208-214.
[6]	Ruan Hongli, Zhang Jingyuan, Sun Sai, Yang Ying, Zhu Xiaolei, Lü Chengwei. N-Bromosuccinimide Mediated the Reaction of 2-Hydroxyaryl Aldehydes with Meldrum's Acid for Synthesis of Coumarin-3-carboxylic Acids [J]. Chin. J. Org. Chem., 2017, 37(8): 2139-2144.
[7]	Zan Ningning, Zhang Yulei, Zhang Shuai, Liu Si, Jiang Lin. Synthesis of Novel 3,3-Dimethyl-1-(pyridin-3-yl) butan-2-one Oxime Esters and Evaluation of Their Antifungal Activity [J]. Chin. J. Org. Chem., 2017, 37(10): 2767-2771.
[8]	Zhang Xiaoxiang, Sun Xiaoping, Rao Weidong. Triflic Acid-Catalyzed Tandem Reactions of Cyclopropyl Alcohols with Sulfonamides for the Synthesis of Pyrrolidines [J]. Chin. J. Org. Chem., 2015, 35(7): 1500-1505.
[9]	Li Qingfang, Li Rui, Li Xueqiang, Gu Peiming. Preparation of Aryl Fused Pyrrolizidines via Intramolecular Schmidt Reaction of Acyl Chlorides with Alkyl Azides [J]. Chin. J. Org. Chem., 2015, 35(11): 2326-2332.
[10]	Duan Xinfang;Yin Chenglie. Asymmetric reduction of chiral titanium complexes of α-keto aromatic acids with lithium dialkyl amides [J]. Chin. J. Org. Chem., 2002, 22(1): 64-66.
[11]	SHI ZHEN;GU HUAN. The novel synthetic method of α-hydroxy-aldehydes [J]. Chin. J. Org. Chem., 1997, 17(2): 162-164.
[12]	LIU HANXING;YAN CHENGLIE. Some rules about the exchange reactions between Ti(OR)4 and some alcohols as well as their derivatives [J]. Chin. J. Org. Chem., 1989, 9(5): 417-422.

金催化2-炔基芳基叠氮与羧酸串联反应合成3-吲哚酯

Gold-Catalyzed Tandem Reactions of 2-Alkynyl Arylazides and Carboxylic Acids for the Synthesis of 1H-Indol-3-yl Esters

PDF

Supporting Info.

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 12

Recommended Articles

Metrics

Comments