Palladium-Catalyzed Synthesis of 1H-Indol-3-yl Acrylates from 2-Alkynyl Arylazides and Acrylic Acids

doi:10.6023/cjoc202101047

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (8): 3235-3241.DOI: 10.6023/cjoc202101047 Previous Articles Next Articles

ARTICLES

钯催化2-炔基芳基叠氮与丙烯酸衍生物反应合成1H-吲哚-3-丙烯酸酯

李萍, 周志强, 杨帆, 徐瑶, 张小祥^*()

南京林业大学化学工程学院江苏省林业资源高效加工利用协同创新中心南京210037

收稿日期:2021-01-27 修回日期:2021-04-10 发布日期:2021-05-08
通讯作者: 张小祥
基金资助:
国家自然科学基金(21302096); 江苏省自然科学基金(BK20171449); 国家一流学科资助项目

Palladium-Catalyzed Synthesis of 1H-Indol-3-yl Acrylates from 2-Alkynyl Arylazides and Acrylic Acids

Ping Li, Zhiqiang Zhou, Fan Yang, Yao Xu, Xiaoxiang Zhang()

Jiansu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037

Received:2021-01-27 Revised:2021-04-10 Published:2021-05-08
Contact: Xiaoxiang Zhang
Supported by:
National Natural Science Foundation of China(21302096); Natural Science Foundation of Jiangsu Province(BK20171449); National First-class Disciplines(PNFD)

1. .pdf(1337KB)

Abstract

Cite this article

Ping Li, Zhiqiang Zhou, Fan Yang, Yao Xu, Xiaoxiang Zhang. Palladium-Catalyzed Synthesis of 1H-Indol-3-yl Acrylates from 2-Alkynyl Arylazides and Acrylic Acids[J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3235-3241.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 5

References 12

[1]	(a) Bandini, M.; Eichholzer, A. Angew. Chem., nt. Ed. 2009, 48, 9608.
	(b) Joucla, L.; Djakovitch, L. Adv. Synth. Catal. 2009, 351, 673. doi: 10.1002/adsc.v351:5
	(c) Hong, J.; Xun, L.; Hong, W.; Huashan, Z.; Jieke, C. J. Wuhan Univ. (Nat. Sci. Ed.) 1998, 44, 175.
	(d) Arnold, R. D.; Nutter, W. M.; Stepp, W. L. J. Org. Chem. 1959, 24, 117. doi: 10.1021/jo01083a610
	(e) Liu, K.; Wen, P.; Liu, J.; Huang, G. Synthesis 2010, 3623.
	(f) Pohanka, M.; Drtinova, L. Talanta 2013, 106, 281. doi: 10.1016/j.talanta.2012.10.085
	(g) Li, X.; Yu, L.-M.; Wang, B.-J.; Xia, S.-W.; Zhao, H.-Z. Acta Chim. Sinica 2008, 66, 2507. (in Chinese)
	(李霞, 于良民, 王宝娟, 夏树伟, 赵海洲, 化学学报, 2008, 66, 2507.)
[2]	(a) Sassano, M. F.; Schlesinger, A. P.; Jarstfer, M. B. Open Med. Chem. J. 2012, 6, 20. doi: 10.2174/1874104501206010020 pmid: 11674076
	(b) Masterova, N. S.; Ryabova, S. Y.; Alekseeva, L. M.; Evstratova, M. I.; Kiselev, S. S.; Granik, V. G. Russ. Chem. Bull. 2010, 59, 637. doi: 10.1007/s11172-010-0115-2 pmid: 11674076
	(c) Dorjsuren, D.; Burnette, A.; Gray, G. N.; Chen, X.; Zhu, W.; Roberts, P. E.; Currens, M. J.; Shoemaker, R. H.; Ricciardi, R. P.; Sei, S. Antiviral Res. 2006, 69, 9. doi: 10.1016/j.antiviral.2005.09.005 pmid: 11674076
	(d) Perlmutter, P.; Puniani, E.; Westman, G. Tetrahedron Lett. 1996, 37, 1715. doi: 10.1016/0040-4039(96)00115-3 pmid: 11674076
	(e) Krajnc, P.; Štefanec, D.; Brown, J. F.; Cameron, N. R. J. Polym. Sci., art A: Polym. Chem. 2005, 43, 296. pmid: 11674076
	(f) Štefanec, D.; Krajnc, P. Polym. Inter. 2007, 56, 1313. doi: 10.1002/(ISSN)1097-0126 pmid: 11674076
	(g) Vasconcellos, M. L.; Silva, T. M.; Camara, C. A. Pest. Manage. Sci. 2006, 62, 288. doi: 10.1002/(ISSN)1526-4998 pmid: 11674076
	(h) Littke, A. F.; Fu, G. C. J. Org. Chem. 1999, 64, 10. pmid: 11674076
[3]	(a) Pohanka, M.; Drtinova, L. Talanta 2013, 106, 281. doi: 10.1016/j.talanta.2012.10.085
	(b) Nirogia, R. V. S.; Kambhampati, R.; Daulatabad, A. V.; Gudla, P.; Shaikh, M.; Achanta, P. K.; Shinde, A. K.; Dubey, P. K. J. Enzyme Inhib. Med. Chem. 2011, 26, 341. doi: 10.3109/14756366.2010.510471
[4]	Gherbovet, O.; Fauré, R.; Ferreira, F.; Durand, J.; Ragon, M.; Hostyn, G.; Record, E.; Bozonnet, S.; O’Donohue, M. J. J. Mol. Catal. B: Enzym. 2016, 126, 24. doi: 10.1016/j.molcatb.2016.01.012
[5]	Song, J.; Cui, J.; Liang, H.-B.; Liu, Q.; Dong, Y.-H.; Liu, H. Asian J. Org. Chem. 2018, 7, 341. doi: 10.1002/ajoc.v7.2
[6]	Zhu, J.-D.; Fang, S.-S.; Sun, K.-W.; Fang, C.; Lu, T.; Du, D. J. Org. Chem. 2018, 83, 10430. doi: 10.1021/acs.joc.8b01488
[7]	(a) Li, P.; Zhu, B.; Xu, Y.; Zhou, Z.; Hu, G.; Yang, F.; Xu, S.; Zhang, X. Org. Chem. Front. 2020, 7, 3480. doi: 10.1039/D0QO00799D
	(b) Li, P.; Yong, W.; Sheng, R.; Rao, W.; Zhu, X.; Zhang, X. Adv. Synth. Catal. 2019, 361, 201. doi: 10.1002/adsc.v361.1
[8]	For recent selected examples of α-imino metal carbenes from 2-alkynyl arylazides: pmid: 23909764
	(a) Lu, B.; Luo, Y.-D.; Liu, L.-Z.; Ye, L.-W.; Wang, Y.-Z.; Zhang, L.-M. Angew. Chem., nt. Ed. 2011, 50, 8358. pmid: 23909764
	(b) Wetzel, A.; Gagosz, F. Angew. Chem., nt. Ed. 2011, 50, 7354. pmid: 23909764
	(c) Hou, Z.; Oishi, S.; Suzuki, Y.; Kure, T.; Nakanishi, I.; Hirasawa, A.; Tsujimoto, G.; Ohno, H.; Fujii, N. Org. Biomol. Chem. 2013, 11, 3288. doi: 10.1039/c3ob40223a pmid: 23909764
	(d) Tokimizu, Y.; Oishi, S.; Fujii, N.; Ohno, H. Org. Lett. 2014, 16, 3138. doi: 10.1021/ol5012604 pmid: 23909764
	(e) Zhou, Q.; Zhang, Z.; Zhou, Y.; Li, S.; Zhang, Y.; Wang, J. J. Org. Chem. 2017, 82, 48. doi: 10.1021/acs.joc.6b01864 pmid: 23909764
	(f) Li, T.; Chen, B.-L.; Zhu, L.-L.; Chen, Z. Tetrahedron Lett. 2020, 61, 151851. doi: 10.1016/j.tetlet.2020.151851 pmid: 23909764
	(g) Li, N.; Lian, X.-L.; Li, Y.-H.; Wang, T.-Y.; Han, Z.-Y.; Zhang, L.; Gong, L.-Z. Org. Lett. 2016, 18, 4178. doi: 10.1021/acs.orglett.6b01627 pmid: 23909764
	(h) Gronnier, C.; Boissonnat, G.; Gagosz, F. Org. Lett. 2013, 15, 4234. doi: 10.1021/ol4019634 pmid: 23909764
	(i) Shen, W.-B.; Sun, Q.; Li, L.; Liu, X.; Zhou, B.; Yan, J.-Z.; Lu, X.; Ye, L.-W. Nat. Commun. 2017, 8, 1748. doi: 10.1038/s41467-017-01853-1 pmid: 23909764
	For recent selected examples of metal carbenes: pmid: 23909764
	(j) Li, M.-L; Chen, M.-Q.; Xu, B.; Zhu, S.-F.; Zhou, Q.-L. Acta Chim. Sinica 2018, 76, 883. (in Chinese) doi: 10.6023/A18060234 pmid: 23909764
	(李茂霖, 陈梦青, 徐彬, 朱守非, 周其林, 化学学报, 2018, 76, 883.) doi: 10.6023/A18060234 pmid: 23909764
	(k) Qiu, D.; Qiu, M.-L.; Ma, R.; Zhang, Y.; Wang, J.-B. Acta Chim. Sinica 2016, 74, 472. (in Chinese) doi: 10.6023/A16030153 pmid: 23909764
	(邱頔, 邱孟龙, 马戎, 张艳, 王剑波, 化学学报, 2016, 74, 472.) doi: 10.6023/A16030153 pmid: 23909764
[9]	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.) doi: 10.6023/cjoc201501020
[10]	Zhang, X.-X.; Li, P.; Lyu, C.; Yong, W.-X.; Li, J.; Zhu, X.-B.; Rao, W.-D. Org. Biomol. Chem. 2017, 15, 6080. doi: 10.1039/C7OB01337J
[11]	(a) Zhang, X.-X.; Sun, X.-P.; Fan, H.; Li, P.; Lyu, C.; Rao, W.-D. Eur. J. Org. Chem. 2016, 25, 426.
	(b) Zhang, X.-X.; Sun, X.-P.; Fan, H.; Lyu, C.; Li, P.; Zhang, H.-F.; Rao, W.-D. RSC Adv. 2016, 6, 56319. doi: 10.1039/C6RA09761H
[12]	For recent selected examples on the generation of palladium carbenes:
	(a) Ding, H.; Bai, S.; Lu, P.; Wang, Y. Org. Lett. 2017, 19, 4604. doi: 10.1021/acs.orglett.7b02211
	(b) Shao, Z.; Zhang, H. Chem. Soc. Rev. 2012, 41, 560. doi: 10.1039/C1CS15127D
	(c) Xiao, Q.; Zhang, Y.; Wang, J. Acc. Chem. Res. 2013, 46, 236. doi: 10.1021/ar300101k
	(d) Xia, Y.; Zhang, Y.; Wang, J. ACS Catal. 2013, 3, 2586. doi: 10.1021/cs4006666
	(e) Liu, Z.; Tan, H.; Fu, T.; Xia, Y.; Qiu, D.; Zhang, Y.; Wang, J. J. Am. Chem. Soc. 2015, 137, 12800. doi: 10.1021/jacs.5b09135

Entry	Catalyst	Solvent	Time/h	Yield^b/%
1	Pd(OAc)₂	DCE	2	91
2	PdCl₂	DCE	6	59
3	PdCl₂(PPh₃)₂	DCE	6	20
4	Pd(NO₃)₂•2H₂O	DCE	1	70^c
5	Pd(PPh₃)₄	DCE	6	36
6	Pd(OAc)₂	DCE	3	91^d
7	Pd(OAc)₂	DCE	6	70^e
8	Pd(OAc)₂	DCE	18	72^c
9	Pd(OAc)₂	DCE	2	82^f
10	Pd(OAc)₂	PhCl	3	83
11	Pd(OAc)₂	MeCN	3	75
12	—	DCE	24	NR^g

Entry	Catalyst	Solvent	Time/h	Yield^b/%
1	Pd(OAc)₂	DCE	2	91
2	PdCl₂	DCE	6	59
3	PdCl₂(PPh₃)₂	DCE	6	20
4	Pd(NO₃)₂•2H₂O	DCE	1	70^c
5	Pd(PPh₃)₄	DCE	6	36
6	Pd(OAc)₂	DCE	3	91^d
7	Pd(OAc)₂	DCE	6	70^e
8	Pd(OAc)₂	DCE	18	72^c
9	Pd(OAc)₂	DCE	2	82^f
10	Pd(OAc)₂	PhCl	3	83
11	Pd(OAc)₂	MeCN	3	75
12	—	DCE	24	NR^g

[1]	Xiaoyu Lu, Xiaomei Sun, Yaqing Niu, Junchao Wang, Wenjing Yin, Mengting Gao, Zi Liu, Zhenghuan Wei, Tinghua Tao. Copper-Catalyzed Decarboxylative Cross-Coupling of α‑Fluoroacrylic Acids with N-Tosyl Oxaziridines [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2110-2119.
[2]	Youcai Zhu, Xinxin Ding, Li Sun, Zhen Liu. Advances in the Production of Acrylic Acid and Its Derivatives by CO₂/C₂H₄ Coupling [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 965-977.
[3]	Shang Xiaojie, Liu Zhongquan. Recent Developments in Pd-Catalyzed Oxidative Heck Cross Coupling Reaction of Arenes/Alkenes with Allylic Esters [J]. Chin. J. Org. Chem., 2015, 35(3): 522-527.
[4]	MA Yuan-Hui,ZHANG Yong-Jian,ZHANG Wan-Bin*. Progress in Catalytic Asymmetric Hydrogenation of β-Aminoacrylic Acid Derivatives [J]. Chin. J. Org. Chem., 2007, 27(03): 289-297.
[5]	WANG, Yong, YIN, Han-Dong, WANG, Chuan-Hua, MA, Chun-Lin. Synthesis and Characterization of {[(n-Bu)₂Sn (O₂CCHCHAr)]₂O}₂ and Crystal Structure of {[(n-Bu)₂Sn (O₂CCHCHPh)]₂O}₂ [J]. Chinese Journal of Organic Chemistry, 2004, 24(4): 414-418.
[6]	LIU Pu, WANG Lan, LI Li-Min, WANG Xiang-Yu. Study on the Heck Arylation Reaction Catalyzed by Chitosan-immobilized Palladium(0) Complex [J]. Chinese Journal of Organic Chemistry, 2004, 24(1): 59-62.
[7]	Cai Mingzhong;Zhao Hong;Huang Yizheng. Synthesis of Poly-4-oxa-6,7-dimethylselenoheptylsiloxane Palladium (O) Complex and Its Catalytic Properties [J]. Chin. J. Org. Chem., 2003, 23(6): 555-558.
[8]	Liu Liu;Zhang Haitao;Wang Yunpu. Studies on the Interaction of Water-Soluble Polymer-Supported Ferrocenyl Schiff Base with DNA [J]. Chin. J. Org. Chem., 2003, 23(6): 570-573.
[9]	Dyab Zgufang;Xie Wenlin;Huang Zhishu;Ma Lin;Gu Lianquan. Synthesis of bis(3-phenyl-2propenoyl) substituted thioureas and bis (3-phenyl-2-propenoyl) substituted amines using phase transfer catalysis [J]. Chin. J. Org. Chem., 2002, 22(9): 681-684.
[10]	Liu Liu;Zhang Haitao;Wang Yunpu. Syntheses of water-soluble polymer-supported ferrocenyl schiff bases [J]. Chin. J. Org. Chem., 2002, 22(4): 286-288.
[11]	JIANG WEIPING;SHI YAOZENG;LU WANFANG;HU HONGWEN. Studies on the synthesis of amino acids VI: Condensation of N-cyanomethylbenzenecarboximidoate and aromatic aldehydes [J]. Chin. J. Org. Chem., 1989, 9(4): 340-343.
[12]	CHEN QINGHUA;XIE MENGXIA;JIA XIBEI;WANG XUELIANG. Studies on intramolecular 1,3-dipolar cycloaddition reactions IV: The thermochemical and photochemical reactions of some 1,3-dipolar nitrone systems and related regioselectivities [J]. Chin. J. Org. Chem., 1989, 9(2): 156-162.
[13]	XU JIANHUA;TAN LUSHI;HU HONGWEN. Li2 PdCI4-CuCI catalyzed reactions of arenediazonium salts with methyl acrylic acid [J]. Chin. J. Org. Chem., 1987, 7(6): 452-454.
[14]	YUE CHONGWEI;LI ZHENGHUA. Syntheses of 4-carbamoylimidazole-5-hydroxyl substituted \a\-methylcinnamates [J]. Chin. J. Org. Chem., 1986, 6(6): 443-446.
[15]	LIU ZHUJIN;WU HOUMING;XU YONGZHEN;MIN YAOLAN;LI AIFANG;FU GUIXIANG. Study on the composition of the floral absolute oil of elaeagnus angustifolia Linn [J]. Chin. J. Org. Chem., 1986, 6(4): 301-304.

钯催化2-炔基芳基叠氮与丙烯酸衍生物反应合成1H-吲哚-3-丙烯酸酯

Palladium-Catalyzed Synthesis of 1H-Indol-3-yl Acrylates from 2-Alkynyl Arylazides and Acrylic Acids

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 5

References 12

Related Articles 15

Recommended Articles

Metrics

Comments