Dirhodium/Xantphos-Catalyzed Tandem C—H Functionalization/Allylic Alkylation: Direct Access to 3-Acyl-3-allyl Oxindole Derivatives from N-Aryl-α-diazo-β-keto Amides

doi:10.6023/cjoc202206053

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (10): 3390-3397.DOI: 10.6023/cjoc202206053 Previous Articles Next Articles

Special Issue: 不对称催化专辑

ARTICLES

双铑(II)/Xantphos催化的C—H官能团化/烯丙基烷基化串联: 从N-芳基-α-重氮-β-酮酯简便制备3-酰基-3-烯丙基氧化吲哚衍生物

李芳洁^a^,^b, 卢斌^b, 刘阳^a^,^*(), 王晓明^b^,^c^,^*()

a 肿瘤微环境响应药物研究湖南省重点实验室湖南省分子靶标新药研究南华大学衡阳医学院药学院协同创新中心湖南衡阳 421001
b 中国科学院上海有机化学研究所金属有机化学国家重点实验室分子合成科学卓越创新中心上海 200032
c 中国科学院大学杭州高等研究院化学与材料科学学院杭州 310024

收稿日期:2022-06-28 修回日期:2022-08-26 发布日期:2022-11-02
通讯作者: 刘阳, 王晓明
基金资助:
国家自然科学基金(21821002)

Dirhodium/Xantphos-Catalyzed Tandem C—H Functionalization/Allylic Alkylation: Direct Access to 3-Acyl-3-allyl Oxindole Derivatives from N-Aryl-α-diazo-β-keto Amides

Fangjie Li^a^,^b, Bin Lu^b, Yang Liu^a(), Xiaoming Wang^b^,^c()

a Hunan Provincial Key Laboratory of Tumor Microenvironment Responsive Drug Research, Hunan Province Cooperative Innovation Center for Molecular Target New Drug Study, School of Pharmacology, Hengyang Medical School, University of South China, Hengyang, Hunan 421001
b State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
c School of Chemistry and Materials Science, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, Hangzhou 310024

Received:2022-06-28 Revised:2022-08-26 Published:2022-11-02
Contact: Yang Liu, Xiaoming Wang
Supported by:
National Natural Science Foundation of China(21821002)

1. .pdf(1822KB)

Abstract

A novel [Rh₂]/Xantphos-catalyzed one-pot sequence for the synthesis of diverse 3-acyl-3-allyl oxindole derivatives from easily available N-aryl-α-diazo-β-keto amides and allylic compounds has been developed. The notable features of this work include ease of operation, mild reaction conditions, good functional group compatibility and facile diversification of the products. Preliminary mechanistic studies indicate a tandem carbene-induced C—H functionalization and Rh(II)/Xantphos catalyzed allylic alkylation process. Moreover, the choice of Xantphos as the ligand is critical to enable the allylic alkylation process in this catalysis.

Key words: dirhodium(II), diazo compounds, oxindoles, quaternary centers, relay catalysis

Cite this article

Fangjie Li, Bin Lu, Yang Liu, Xiaoming Wang. Dirhodium/Xantphos-Catalyzed Tandem C—H Functionalization/Allylic Alkylation: Direct Access to 3-Acyl-3-allyl Oxindole Derivatives from N-Aryl-α-diazo-β-keto Amides[J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3390-3397.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 8

References 15

[1]	(a) Galliford, C. V.; Scheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 8748. doi: 10.1002/anie.200701342
	(b) Yu, B.; Yu, D.-Q.; Liu, H.-M. Eur. J. Med. Chem. 2015, 97, 673. doi: 10.1016/j.ejmech.2014.06.056
[2]	(a) Zhou, F.; Liu, Y.-L.; Zhou, J. Adv. Synth. Catal. 2010, 352, 1381. doi: 10.1002/adsc.201000161 pmid: 22899437
	(b) Dalpozzo, R.; Bartoli, G.; Bencivenni, G. Chem. Soc. Rev. 2012, 41, 7247. doi: 10.1039/c2cs35100e pmid: 22899437
	(c) Liu, Y.-L.; Wang, X.; Zhao, Y.-L.; Zhu, F.; Zeng, X.-P.; Chen, L.; Wang, C.-H.; Zhao, X.-L.; Zhou, J. Angew. Chem., Int. Ed. 2013, 52, 13735. doi: 10.1002/anie.201307250 pmid: 22899437
	(d) Cao, Z.-Y.; Wang, X.; Tan, C.; Zhao, X.-L.; Zhou, J.; Ding, K. J. Am. Chem. Soc. 2013, 135, 8197. doi: 10.1021/ja4040895 pmid: 22899437
	(e) Zhou, F.; Tan, C.; Tang, J.; Zhang, Y.-Y.; Gao, W.-M.; Wu, H.-H.; Yu, Y.-H.; Zhou, J. J. Am. Chem. Soc. 2013, 135, 10994. doi: 10.1021/ja4066656 pmid: 22899437
	(f) Zeng, X.-P.; Cao, Z-Y.; Wang, Y.-H.; Zhou, F.; Zhou, J. Chem. Rev. 2016, 116, 7330. doi: 10.1021/acs.chemrev.6b00094 pmid: 22899437
	(g) Cao, Z.-Y.; Zhou, F.; Zhou, J. Acc. Chem. Res. 2018, 51, 1443. doi: 10.1021/acs.accounts.8b00097 pmid: 22899437
	(h) Xu, P.-W.; Yu, J.-S.; Chen, C.; Cao, Z.-Y.; Zhou, F.; Zhou, J. ACS Catal. 2019, 9, 1820. doi: 10.1021/acscatal.8b03694 pmid: 22899437
	(i) Marchese, A. D.; Larin, E. M.; Mirabi, B.; Lautens, M. Acc. Chem. Res. 2020, 53, 1605. doi: 10.1021/acs.accounts.0c00297 pmid: 22899437
	(j) Liu, T. T.; Zhang, X. Y.; Miao, Z. W. Chin. J. Org. Chem. 2021, 41, 3965. (in Chinese). doi: 10.6023/cjoc202104008 pmid: 22899437
	(刘奕彤, 张茜苑, 苗志伟, 有机化学, 2021, 41, 3965.) pmid: 22899437
[3]	(a) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. doi: 10.1021/cr9409804 pmid: 32756671
	(b) Cheng, Q.; Tu, H.-F.; Zheng, C.; Qu, J.-P.; Helmchen, G.; You, S.-L. Chem. Rev. 2019, 119, 1855. doi: 10.1021/acs.chemrev.8b00506 pmid: 32756671
	(c) Butt, N. A.; Zhang, W. Chem. Soc. Rev. 2015, 44, 7929. doi: 10.1039/C5CS00144G pmid: 32756671
	(d) Turnbull, B. W. H.; Evans, P. A. J. Org. Chem. 2018, 83, 11463. doi: 10.1021/acs.joc.8b00583 pmid: 32756671
	(e) Zhang, H.; Gu, Q.; You, S.-L. Chin. J. Org. Chem. 2019, 39, 15. (in Chinese). pmid: 32756671
	(张慧君, 顾庆, 游书力, 有机化学, 2019, 39, 15.) doi: 10.6023/cjoc201809037 pmid: 32756671
	(f) Huang, H.-M.; Bellotti, P.; Glorius, F. Chem. Soc. Rev. 2020, 49, 6186. doi: 10.1039/d0cs00262c pmid: 32756671
[4]	(a) Wei, F.; Song, C.-L.; Ma, Y.-D.; Zhou, L.; Tung, C.-H.; Xu, Z.-H. Sci. Bull. 2015, 60, 1479. doi: 10.1007/s11434-015-0874-0 pmid: 26658761
	(b) Liu, .; Zhang, J.-L. Chem. Soc. Rev. 2016, 45, 506. doi: 10.1039/c5cs00821b pmid: 26658761
[5]	For selected examples, see: a , Qiu, H.; Li, M.; Jiang, L.-Q.; Lv, F.-P.; Zan, L.; Zhai, C.-W.; Doyle, M. P.; Hu, W.-H. Nat. Chem. 2012, 4, 733. doi: 10.1038/nchem.1406 pmid: 35756859
	(b) Xi, Y.; Su, Y.; Yu, Z.; Dong, B.; McClain, E. J.; Lan, Y.; Shi, X. Angew. Chem., Int. Ed. 2014, 53, 9817. doi: 10.1002/anie.201404946 pmid: 35756859
	(c) Yu, Z.; Ma, B.; Chen, M.; Wu, H.-H.; Liu, L.; Zhang, J. J. Am. Chem. Soc. 2014, 136, 6904. doi: 10.1021/ja503163k pmid: 35756859
	(d) Chen, D.-F.; Zhao, F.; Hu, Y.; Gong, L.-Z. Angew. Chem., Int. Ed. 2014, 53, 10763. doi: 10.1002/anie.201406098 pmid: 35756859
	(e) Chen, D.-F.; Zhang, C.-l.; Hu, Y.; Han, Z.-Y.; Gong, L.-Z. Org. Chem. Front. 2015, 2, 956. doi: 10.1039/C5QO00151J pmid: 35756859
	(f) Jing C.; Xing, D.; Hu, W. Org. Lett. 2015, 17, 4336. doi: 10.1021/acs.orglett.5b02160 pmid: 35756859
	(g) Xu, B.; Li, ML.; Zuo, X.-D.; Zhu, S.-F.; Zhou, Q.-L. J. Am. Chem. Soc. 2015, 137, 8700. doi: 10.1021/jacs.5b05086 pmid: 35756859
	(h) Yu, Z.; Li, Y.; Shi, J.; Ma, B.; Liu, L.; Zhang, J. Angew. Chem.,Int. Ed. 2016, 55, 14807. doi: 10.1002/anie.201608937 pmid: 35756859
	(i) Fructos, M. R.; Díaz-Requejo M. M.; Pérez P. J. Chem. Commun. 2016, 52, 7326. doi: 10.1039/C6CC01958G pmid: 35756859
	(j) Ma, B.; Chu, Z.; Huang, B.; Liu, Z.; Liu, L.; Zhang, J. Angew. Chem., Int. Ed. 2017, 56, 2749. doi: 10.1002/anie.201611809 pmid: 35756859
	(k) Fructos, M. R.; Besora, M.; Braga, A. A. C.; Díaz-Requejo, M. M.; Maseras, F.; Perez, P. J. Organometallics 2017, 36, 172. doi: 10.1021/acs.organomet.6b00604 pmid: 35756859
	(l) Kang, Z.; Zhang, D.; Xu, X.; Hu, W. Org. Lett. 2019, 21, 9878. doi: 10.1021/acs.orglett.9b03787 pmid: 35756859
	(m) Yu, Z.; Li, Y.; Zhang, P.; Liu, L.; Zhang, J. Chem. Sci. 2019, 10, 6553. doi: 10.1039/C9SC01657K pmid: 35756859
	(n) Jana, S.; Empel, C.; Pei, C.; Aseeva, P.; Nguyen, T. V.; Koenigs, R. M. ACS Catal. 2020, 10, 9925. doi: 10.1021/acscatal.0c02230 pmid: 35756859
	(o) Zhang, C.; Hong, K.; Pei, C.; Zhou, S.; Hu, W.; Hashmi, A. S. K.; Xu, X. Nat. Commun. 2021, 12, 1182. doi: 10.1038/s41467-021-21335-9 pmid: 35756859
	(p) Zhu, D.-X.; Xia, H.; Liu, J.-G.; Chung, L.-W.; Xu, M.-H. J. Am. Chem. Soc. 2021, 143, 2608. doi: 10.1021/jacs.0c13191 pmid: 35756859
	(q) Li, Z.; Chen, Y.; Wang, C.; Xu, G.; Shao, Y.; Zhang, X.; Sun, J. Angew. Chem., Int. Ed. 2021, 60, 25714. doi: 10.1002/anie.202110430 pmid: 35756859
	(r) Pizarro, J. D.; Schmidtke, I. L.; Nova, A.; Fructos, M. R.; Pérez, P. J. ACS Catal. 2022, 12, 6851. doi: 10.1021/acscatal.2c01713 pmid: 35756859
	(s) Jia, S.; Xing, D.; Zhang, D.; Hu, W. Angew. Chem., Int. Ed. 2014, 53, 13098. doi: 10.1002/anie.201406492 pmid: 35756859
[6]	(a) Jing, C.; Xing, D.; Hu, W. Org. Lett. 2015, 17, 4336. doi: 10.1021/acs.orglett.5b02160
	(b) Kang, Z.; Zhang, D.; Xu, X.; Hu, W. Org. Lett. 2019, 21, 9878. doi: 10.1021/acs.orglett.9b03787
[7]	(a) Yamamoto, K.; Qureshi, Z.; Tsoung, J.; Pisella, G.; Lautens, M. Org. Lett. 2016, 18, 4954. pmid: 27632781
	(b) Chen, L. H.; Ma, Y. T.; Yang, F.; Huang, X. Y.; Chen, S. W.; Ji, K.; Chen, Z. S. Adv. Synth. Cat. 2019, 361, 1307. doi: 10.1002/adsc.201801346 pmid: 27632781
	(c) Lee, Y. L.; Lee, K. R.; Xuan, Z.; Lee, S.-G. Bull. Korean Chem. Soc. 2021, 42, 537. doi: 10.1002/bkcs.12211 pmid: 27632781
[8]	(a) Tsuji, J.; Minami, I.; Shimizu, I. Tetrahedron Lett. 1984, 25, 5157. doi: 10.1016/S0040-4039(01)81551-3 pmid: 30183287
	(b) Turnbull, B. W. H.; Evans, P. A. J. Org. Chem. 2018, 83, 11463. doi: 10.1021/acs.joc.8b00583 pmid: 30183287
	(c) Thoke, M. B.; Kang, Q. Synthesis 2019, 51, 2585. doi: 10.1055/s-0037-1611784 pmid: 30183287
[9]	(a) Cheng, M.; Huang, X.-Y.; Yang, F.; Zhao, D.-M.; Ji, K.; Chen, Z.-S. Org. Lett. 2022, 24, 1237. doi: 10.1021/acs.orglett.2c00073
	For selected examples of RhII/Pd(0)dual catalyzed two-com- ponent reactions of diazo compounds with allylic compounds, see: (b) Chen, Z.-S.; Huang, X.-Y.; Gao, J.-M.; Ji, K. Org. Lett. 2016, 18, 5876. doi: 10.1021/acs.orglett.6b02958
	(c) Chen, Z.-S.; Huang, X.-Y.; Chen, L.-H.; Gao, J.-M.; Ji, K. ACS Catal. 2017, 7, 7902. doi: 10.1021/acscatal.7b02909
	(d) Huang, L.-Z.; Xuan, Z.; Jeon, H. J.; Du, Z.-T.; Kim, J. H.; Lee, S.-G. ACS Catal. 2018, 8, 7340. doi: 10.1021/acscatal.8b01687
	(e) Wang, X. X.; Huang, X. Y.; Lei, S. H.; Yang, F.; Gao, J. M.; Ji, K.; Chen, Z. S. Chem. Commun. 2020, 56, 782. doi: 10.1039/C9CC08559A
	For an elegant RhII/Pd(0)/chiral phosphoric acid catalyzed three- component allylation of α-diazo carbonyl compounds with alcohols and allyl carbonates, see: (f) Kang, Z.; Chang, W.; Tian, X.; Fu, X.; Zhao, W.; Xu, X.; Liang, Y.; Hu, W. J. Am. Chem. Soc. 2021, 143, 20818. doi: 10.1021/jacs.1c09148
[10]	(a) Lu, B.; Liang, X.; Zhang, J.; Wang, Z.; Peng, Q.; Wang, X. J. Am. Chem. Soc. 2021, 143, 11799. doi: 10.1021/jacs.1c05701
	(b) Yang, Y.; Lu, B.; Xu, G.; Wang, X. ACS Cent. Sci. 2022. 8, 581 doi: 10.1021/acscentsci.2c00004
[11]	For excellent reviews about the axial modification of dirhodium in catalysis, see: (a) Trindade, A. F.; Coelho, J. A. S.; Afonso, C. A. M.; Veiros, L. F.; Gois, P. M. P. ACS Catal. 2012, 2, 370. doi: 10.1021/cs200597a
	(b) Hong, B.; Shi, L.; Li, L.; Zhan, S.; Gu, Z. Green Synth. Catal. 2022. doi.org/10.1016/j.gresc.2022.03.001.
[12]	For selected examples, see: (a) Wang, D.; Zhao, Y.; Yuan, C.; Wen, J.; Zhao, Y.; Shi, Z. Angew. Chem., Int. Ed. 2019, 58, 12529. doi: 10.1002/anie.201906975
	(b) Fu, L.; Li, S.; Cai, Z.; Ding, Y.; Guo, X.-Q.; Zhou, L.-P.; Yuan, D.; Sun, Q.-F.; Li, G. Nat. Catal. 2018, 1, 469. doi: 10.1038/s41929-018-0080-y
	(c) Vora, H. U.; Silvestri, A. P.; Engelin, C. J.; Yu, J. Q. Angew. Chem., Int. Ed. 2014, 53, 2683.
	(d) Kwak, J.; Kim, M.; Chang, S. J. Am. Chem. Soc. 2011, 133, 3780. doi: 10.1021/ja111670s
	(e) Trindade, A. F.; Gois, P. M. P.; Veiros, L. F.; André, V.; Duarte, M. T.; Afonso, C. A. M.; Caddick, S.; Cloke, F. G. N. J. Org. Chem. 2008, 73, 4076. doi: 10.1021/jo800087n
	(f) Gois, P. M. P.; Trindade, A. F.; Veiros, L. F.; André, V.; Duarte, M. T.; Afonso, C. A. M.; Caddick, S.; Cloke, F. G. N. Angew. Chem., Int. Ed. 2007, 46, 5750. doi: 10.1002/anie.200700924
[13]	Moreno-Cabrerizo, C.; Ortega-Martínez, A.; Esteruelas, M. A.; López, A. M.; Nájera, C.; Sansano, J. M. Eur. J. Org. Chem. 2020, 2020, 3101 doi: 10.1002/ejoc.202000375
[14]	Mandal, T.; Chakraborti, G.; Karmakar, S.; Dash, J. Org. Lett. 2018, 20, 4759. doi: 10.1021/acs.orglett.8b01827
[15]	(a) Guo, X.; Hu, W. Acc. Chem. Res. 2013, 46, 2427. doi: 10.1021/ar300340k
	(b) Zhang, D.; Hu, W. Chem. Rec. 2017, 17, 739. doi: 10.1002/tcr.201600124

Entry	[Rh] cat.	Ligand	Base	Solvent	Yield^b/%
Entry	[Rh] cat.	Ligand	Base	Solvent	3a	4a
1	Rh₂(Oct)₄	Xantphos	Cs₂CO₃	DCE	—	51
2	Rh₂(Oct)₄	Xantphos	—	DCE	83	0
3	Rh₂(Oct)₄	Xantphos	KOAc	DCE	—	74
4	Rh₂(Oct)₄	Xantphos	KOAc	PhCF₃	—	88
5	Rh₂(OAc)₄	Xantphos	KOAc	PhCF₃	—	<1
6	Rh₂(TFA)₄	Xantphos	KOAc	PhCF₃	—	7
7	Rh(COD)₂BF₄	Xantphos	KOAc	PhCF₃	N.R.^c	N.R.^c
8	Rh₂(Oct)₄	BINAP	KOAc	PhCF₃	—	9
9	Rh₂(Oct)₄	dppb	KOAc	PhCF₃	—	7
10	Rh₂(Oct)₄	PPh₃	KOAc	PhCF₃	—	<5
11	Rh₂(Oct)₄	ⁱPr-NHC^d	KOAc	PhCF₃	—	<5
12^e	Rh₂(Oct)₄	Xantphos	KOAc	PhCF₃	—	83
13^f	Rh₂(Oct)₄	Xantphos	KOAc	PhCF₃	—	84
14	—	Xantphos	KOAc	PhCF₃	—	N.R.
15	Rh₂(Oct)₄	—	KOAc	PhCF₃	—	N.R.

Entry	[Rh] cat.	Ligand	Base	Solvent	Yield^b/%
Entry	[Rh] cat.	Ligand	Base	Solvent	3a	4a
1	Rh₂(Oct)₄	Xantphos	Cs₂CO₃	DCE	—	51
2	Rh₂(Oct)₄	Xantphos	—	DCE	83	0
3	Rh₂(Oct)₄	Xantphos	KOAc	DCE	—	74
4	Rh₂(Oct)₄	Xantphos	KOAc	PhCF₃	—	88
5	Rh₂(OAc)₄	Xantphos	KOAc	PhCF₃	—	<1
6	Rh₂(TFA)₄	Xantphos	KOAc	PhCF₃	—	7
7	Rh(COD)₂BF₄	Xantphos	KOAc	PhCF₃	N.R.^c	N.R.^c
8	Rh₂(Oct)₄	BINAP	KOAc	PhCF₃	—	9
9	Rh₂(Oct)₄	dppb	KOAc	PhCF₃	—	7
10	Rh₂(Oct)₄	PPh₃	KOAc	PhCF₃	—	<5
11	Rh₂(Oct)₄	ⁱPr-NHC^d	KOAc	PhCF₃	—	<5
12^e	Rh₂(Oct)₄	Xantphos	KOAc	PhCF₃	—	83
13^f	Rh₂(Oct)₄	Xantphos	KOAc	PhCF₃	—	84
14	—	Xantphos	KOAc	PhCF₃	—	N.R.
15	Rh₂(Oct)₄	—	KOAc	PhCF₃	—	N.R.

双铑(II)/Xantphos催化的C—H官能团化/烯丙基烷基化串联: 从N-芳基-α-重氮-β-酮酯简便制备3-酰基-3-烯丙基氧化吲哚衍生物

Dirhodium/Xantphos-Catalyzed Tandem C—H Functionalization/Allylic Alkylation: Direct Access to 3-Acyl-3-allyl Oxindole Derivatives from N-Aryl-α-diazo-β-keto Amides

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 8

References 15

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Xiaoping Xu, Yifei Zhang, Xiaoyu Mo, Jun Jiang. Rh-Catalyzed C—H Functionalization Reaction between 3-Diazoindolin-2-imines and Pyrazolones for the Construction of 3-Pyrazolyl Indoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2519-2527.
[2]	Zhicheng Bao, Muyao Li, Jianbo Wang. Copper-Catalyzed Cross-Coupling of Aryldiazoacetates with Bis[(pinacolato)boryl]methane [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1808-1814.
[3]	Xuechun Zhao, Hui Fan, Yao Xu, Xiaoming Liao, Xiaoxiang Zhang. PPh₃-Mediated Synthesis of 3-Hydroxy-2-oxindoles from o-Alkynylnitrobenzenes [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3997-4002.
[4]	Zhentao Pan, Tong Liu, Yongmin Ma, Jianbo Yan, Ya-Jun Wang. Construction of Quinazolin(thi)ones by Brønsted Acid/Visible-Light Photoredox Relay Catalysis [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2823-2831.
[5]	Honghua Zuo, Fangrui Zhong. Reactivity Modulation of Labile Quinones and Biomimetic Catalytic Transformations [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 665-678.
[6]	Yang Xie, Jun Xuan. Photocatalytic Reactions Involving Diazo Compounds as Radical Precursors [J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4247-4256.
[7]	Ming-Yu Teng, Tao Han, En-He Huang, Long-Wu Ye. Research Progress on Enantioselective Desymmetrization Reactions Involving Metal Carbenes [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3295-3301.
[8]	Qisheng Gao, Qi Jing, Yang Chen, Jing Sun, Mingdong Zhou. Decarboxylative Amidation of Acrylamides with Oxamic Acids [J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 257-265.
[9]	Yitong Liu, Xiyuan Zhang, Zhiwei Miao. Research Progress on the Synthetic Method of Five-Membered Spirooxindole Derivatives at C-3 Position [J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 3965-3982.
[10]	Zhao Zhuanxia, Wang Junjiao, Huang Danfeng, Yang Zheng, Zhao Fangxia, Hu Yongqin, Xu Weigang, Hu Yulai. Study on Tin Powder-Promoted Allylation of 3-Aryl-3-hydroxy-2-oxindoles [J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 2026-2034.
[11]	Guo Xin, Guo Yajun, Kong Dezhi, Lu Huijie, Hua Yuanzhao, Wang Mincan. Efficient Synthesis of Tetrahydrofuran Spirooxindoles via One-Pot Reaction [J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 1999-2007.
[12]	Zhang Shuo, Lou Jianfang, Wang Jiarui, Song Zihe, Peng Dan, Wang Feng, Yan Zhiwang, Cui Shiqi, Liu Yifan, Mu Qiuhong, Li Jinhui. Zn/Y Bimetallic Relay Catalysis: One Pot Intramolecular Cyclo-isomerization/Intermolecular Alder-Ene Reaction toward Oxazole α-Hydroxy Amide Derivatives [J]. Chinese Journal of Organic Chemistry, 2020, 40(3): 704-713.
[13]	Lin Ye, Du Daming. Recent Advances in Squaramide-Catalyzed Asymmetric Cascade Reactions for the Synthesis of Spirooxindoles [J]. Chinese Journal of Organic Chemistry, 2020, 40(10): 3214-3236.
[14]	Liu Jian, Xiao Jie, Mondal Sudipta, Leng Xuebing, Deng Liang. Reactions of Iron(II) Complexes Supported by Tripodal Amido-Phosphine-Amido Ligands with Diazo Compounds [J]. Chinese Journal of Organic Chemistry, 2020, 40(10): 3380-3389.
[15]	Lang Bo, Suleman Muhammad, Lu Ping, Wang Yanguang. Copper(I)-Promoted Trifluoromethylthiolation of 3-Diazoindolin-2-imines with AgSCF₃: Synthesis of 3-((Trifluoromethyl)thio)-2-aminoindoles [J]. Chinese Journal of Organic Chemistry, 2020, 40(10): 3300-3306.