Synthesis and Application of 3-Aryl Substituted Indenyl Phosphines in Suzuki-Miyaura Cross-Coupling Reactions at Low Catalyst Loadings

doi:10.6023/cjoc202603027

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (10): 3983-3988.DOI: 10.6023/cjoc202603027 Previous Articles Next Articles

ARTICLES

3-芳基茚基膦配体的合成及其在低催化剂用量下Suzuki-Miyaura交叉偶联反应中的应用

陈琼^b, 陈歆雨^b, 郭友利^b, 闫梦琪^b, 孟思璇^b, 陈建^b, 袁佳^a^,^b^,^*(), 余广鳌^b^,^*()

^a 武汉纺织大学纺织新材料与先进加工全国重点实验室纺织新材料与先进加工全国重点实验室武汉 430200
^b 华中师范大学化学学院绿色农药全国重点实验室绿色农药全国重点实验室武汉 430079

收稿日期:2026-03-19 修回日期:2026-05-26 发布日期:2026-07-23
通讯作者: 袁佳, 余广鳌
基金资助:
国家自然科学基金(22371084); 国家自然科学基金(21072071); 国家自然科学基金(21472060); 国家自然科学基金(21772058); 高等学校学科创新引智计划（111计划）(B17019); 华中师范大学中央高校基本科研业务费专项资金(CCNU17CG0011); 华中师范大学中央高校基本科研业务费专项资金(CCNU17KYZHSY07); 华中师范大学中央高校基本科研业务费专项资金(CCNU18KYZHSY06)

Synthesis and Application of 3-Aryl Substituted Indenyl Phosphines in Suzuki-Miyaura Cross-Coupling Reactions at Low Catalyst Loadings

Qiong Chen^b, Xinyu Chen^b, Youli Guo^b, Meng-Qi Yan^b, Sixuan Meng^b, Jian Chen^b, Jia Yuan^a^,^b^,^*(), Guang-Ao Yu^b^,^*()

^a State Key Laboratory of New Textile Materials and Advanced Processing, Wuhan Textile University, Wuhan 430200
^b National Key Laboratory of Green Pesticide, College of Chemistry, Central China Normal University, Wuhan 430079

Received:2026-03-19 Revised:2026-05-26 Published:2026-07-23
Contact: Jia Yuan, Guang-Ao Yu
Supported by:
National Natural Science Foundation of China(22371084); National Natural Science Foundation of China(21072071); National Natural Science Foundation of China(21472060); National Natural Science Foundation of China(21772058); Program of Introducing Talents of Discipline to Universities (111 Project)(B17019); Self-Determined Research Funds of Central China Normal University from the Colleges’ Basic Research and Operation of Ministry of Education(CCNU17CG0011); Self-Determined Research Funds of Central China Normal University from the Colleges’ Basic Research and Operation of Ministry of Education(CCNU17KYZHSY07); Self-Determined Research Funds of Central China Normal University from the Colleges’ Basic Research and Operation of Ministry of Education(CCNU18KYZHSY06)

1. .pdf(679KB)

Abstract

Cite this article

Qiong Chen, Xinyu Chen, Youli Guo, Meng-Qi Yan, Sixuan Meng, Jian Chen, Jia Yuan, Guang-Ao Yu. Synthesis and Application of 3-Aryl Substituted Indenyl Phosphines in Suzuki-Miyaura Cross-Coupling Reactions at Low Catalyst Loadings[J]. Chinese Journal of Organic Chemistry, 2026, 46(10): 3983-3988.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 4

References 19

[1]	For selected reviews, see: (a) Martin R.; Buchwald S. L. Acc. Chem. Res. 2008, 41, 1461. doi: 10.1021/ar800036s
	(b) Devendar P.; Qu R.-Y.; Kang W.-M.; He B.; Yang G.-F. J. Agric. Food Chem. 2018, 66, 8914. doi: 10.1021/acs.jafc.8b03792
	(c) Patel I. S.; Ganesan G.; Jain S. Org. Process Res. Dev. 2024, 28, 3464. doi: 10.1021/acs.oprd.4c00027
[2]	For selected reviews, see: (a) Li H.; Seechurn C. C. C. J.; Colacot T. J. ACS Catal. 2012, 2, 1147. doi: 10.1021/cs300082f
	(b) Gildner P. G.; Colacot T. J. Organometallics. 2015, 34, 5497. doi: 10.1021/acs.organomet.5b00567
	(c) Firsan S. J.; Sivakumar V.; Colacot T. J. Chem. Rev. 2022, 122, 16983. doi: 10.1021/acs.chemrev.2c00204
[3]	(a) Gan K. B.; Zhong R.-L.; Zhang Z.-W.; Kwong F. Y. J. Am. Chem. Soc. 2022, 144, 14864. doi: 10.1021/jacs.2c06240
	(b) Tse M. H.; Choy P. Y.; Kwong F. Y. Acc. Chem. Res. 2022, 55, 3688. doi: 10.1021/acs.accounts.2c00587
[4]	(a) Tang W.; Capacci A. G.; Wei X.; Li W.; White A.; Patel N. D.; Savoie J.; Gao J. J.; Rodriguez S.; Qu B.; Haddad N.; Lu B. Z.; Krishnamurthy D.; Yee N. K.; Senanayake C. H. Angew. Chem., Int. Ed. 2010, 49, 5879. doi: 10.1002/anie.v49:34
	(b) Li C.; Chen T.; Li B.; Xiao G.; Tang W. Angew. Chem., Int. Ed. 2015, 54, 3792. doi: 10.1002/anie.v54.12
	(c) Zhao Q.; Li C.; Senanayake C. H.; Tang W. Chem.-Eur. J. 2013, 19, 2261. doi: 10.1002/chem.v19.7
	(d) Qu B.; Haddad N.; Rodriguez S.; Sieber J. D.; Desrosiers J.-N.; Patel N. D.; Zhang Y.; Grinberg N.; Lee H.; Ma S.; Ries U. J.; Yee N. K.; Senanayake C. H. J. Org. Chem. 2016, 81, 745. doi: 10.1021/acs.joc.5b02368
	(e) Patel N. D.; Rivalti D.; Buono F. G.; Chatterjee A.; Qu B.; Braith S.; Desrosiers J.-N.; Rodriguez S.; Sieber J. D.; Haddad N.; Fandrick K. R.; Lee H.; Yee N. K.; Busacca C. A.; Senanayake C. H. Asian J. Org. Chem. 2017, 6, 1285. doi: 10.1002/ajoc.v6.9
[5]	Stambuli J. P.; Kuwano R.; Hartwig J. F. Angew. Chem., Int. Ed. 2002, 41, 4746. doi: 10.1002/anie.v41:24
[6]	Schaarschmidt D.; Lang H. ACS Catal. 2011, 1, 411. doi: 10.1021/cs200065v
[7]	(a) Yan M.-Q.; Yuan J.; Lan F.; Zeng S.-H.; Gao M.-Y.; Liu S.-H.; Chen J.; Yu G.-A. Org. Biomol. Chem. 2017, 15, 3924. doi: 10.1039/C7OB00178A pmid: 27116077
	(b) Liu Y.; Peng H.; Yuan J.; Yan M.-Q.; Luo X.; Wu Q.-G.; Liu S.-H.; Chen J.; Yu G.-A. Org. Biomol. Chem. 2016, 14, 4664. doi: 10.1039/c6ob00096g pmid: 27116077
	(c) Yuan J.; Zhang Y.; Yu H.; Wang C.; Meng S.; Chen J.; Yu G.-A.; Che C.-M. Org. Biomol. Chem. 2022, 20, 485. doi: 10.1039/D1OB01884A pmid: 27116077
	(d) Chen Y.; Meng T.; Guo R.; Liu Z.; Meng S.; Chen J.; Yu G.-A. Adv. Agrochem 2024, 3, 256. doi: 10.1016/j.aac.2024.06.002 pmid: 27116077
[8]	(a) Xu M.-Y.; Jiang W.-T.; Li Y.; Xu Q.-H.; Zhou Q.-L.; Yang S.; Xiao B. J. Am. Chem. Soc. 2019, 141, 7582. doi: 10.1021/jacs.9b02776
	(b) Wang C.; Liu Y.-C.; Xu M.-Y.; Xiao B. Org. Lett. 2021, 23, 4593. doi: 10.1021/acs.orglett.1c01289
[9]	(a) Chai W.; Zhou Q.; Ai W.; Zheng Y.; Qin T.; Xu X.; Zi W. J. Am. Chem. Soc. 2021, 143, 3595. doi: 10.1021/jacs.0c13412
	(b) Lü Y.; Liao H.; Tang W. Chin. J. Org. Chem. 2024, 44, 3720 (in Chinese). doi: 10.6023/cjoc202408013
	(吕逸文, 廖海华, 汤文军, 有机化学, 2024, 44, 3720.) doi: 10.6023/cjoc202408013
	(c) Wang N.; Tang W. Chin. J. Org. Chem. 2025, 45, 3351 (in Chinese). doi: 10.6023/cjoc202506005
	(王楠, 汤文军, 有机化学, 2025, 45, 3351.) doi: 10.6023/cjoc202506005
	(d) Yu H.; Guan M.; Tong Q.; Jia L.; Jin Z.; Shi J. Chin. J. Org. Chem. 2011, 31, 1100 (in Chinese).
	(于宏伟, 官旻, 童庆松, 贾莉, 金子林, 施继成, 有机化学, 2011, 31, 1100.)
[10]	(a) Wang B. Coord. Chem. Rev. 2006, 250, 242. doi: 10.1016/j.ccr.2005.05.012
	(b) Stradiotto M.; McGlinchey M. J. Coord. Chem. Rev. 2001, 219-221, 311. doi: 10.1016/S0010-8545(01)00339-3
	(c) Kharitonov V. B.; Muratov D. V.; Loginov D. A. Coord. Chem. Rev. 2019, 399, 213027. doi: 10.1016/j.ccr.2019.213027
[11]	(a) Veiros L. F. Organometallics 2000, 19, 3127. doi: 10.1021/om000195j pmid: 11857701
	(b) Calhorda M. J.; Romão C. C.; Veiros L. F. Chem.-Eur. J. 2002, 8, 868. pmid: 11857701
[12]	Yuan J.; Sun Y.; Yu G.-A.; Zhao C.; She N.-F.; Mao S.-L.; Huang P.-S.; Han Z.-J.; Yin J.; Liu S.-H. Dalton Trans. 2012, 41, 10309. doi: 10.1039/c2dt30499f pmid: 22806176
[13]	Stradiotto M.; Cipot J.; McDonald R. J. Am. Chem. Soc. 2003, 125, 5618. pmid: 12733885
[14]	Zhou C.; Chen X.-P.; Lu P.; Wang Y.-G. Tetrahedron 2012, 68, 2844. doi: 10.1016/j.tet.2012.01.093
[15]	Lian Z.-Y.; Yuan J.; Yan M.-Q.; Liu Y.; Luo X.; Wu Q.-G.; Liu S.-H.; Chen J.; Zhu X.-L.; Yu G.-A. Org. Biomol. Chem. 2016, 14, 10090. doi: 10.1039/C6OB01675H
[16]	Chen L.; Yu G.-A.; Li F.; Zhu X.; Zhang B.; Guo R.; Li X.; Yang Q.; Jin S.; Liu C.; Liu S.-H. J. Organomet. Chem. 2010, 695, 1768. doi: 10.1016/j.jorganchem.2010.04.005
[17]	Chen Y.; Peng H.; Pi Y.-X.; Meng T.; Lian Z.-Y.; Yan M.-Q.; Liu Y.; Liu S.-H.; Yu G.-A. Org. Biomol. Chem. 2015, 13, 3236. doi: 10.1039/c4ob02436b pmid: 25639213
[18]	Barder T. E.; Buchwald S. L. J. Am. Chem. Soc. 2007, 129, 5096. doi: 10.1021/ja0683180
[19]	(a) Hunjan M. K.; Panday S.; Gupta A.; Bhaumik J.; Das P.; Laha J. K. Chem. Rec. 2021, 21, 715. doi: 10.1002/tcr.v21.4 pmid: 27689804
	(b) Ruiz-Castillo P.; Buchwald S. L. Chem. Rev. 2016, 116, 12564. pmid: 27689804

Entry	x	Ligand	y	Yield^b/%	TON^c
1	0.01	L1	0.02	<5	—
2	0.02	L1	0.04	79	3950
3	0.05	L1	0.1	82	1640
4	0.01	L2	0.02	57	5700
5	0.02	L2	0.04	86	4300
6	0.05	L2	0.1	86	1720
7	0.01	L3	0.02	36	3600
8	0.02	L3	0.04	78	3900
9	0.05	L3	0.1	85	1700
10	0.01	L4	0.02	<1	—
11	0.02	L4	0.04	<1	—
12	0.05	L4	0.1	<5	—

Entry	x	Ligand	y	Yield^b/%	TON^c
1	0.01	L1	0.02	<5	—
2	0.02	L1	0.04	79	3950
3	0.05	L1	0.1	82	1640
4	0.01	L2	0.02	57	5700
5	0.02	L2	0.04	86	4300
6	0.05	L2	0.1	86	1720
7	0.01	L3	0.02	36	3600
8	0.02	L3	0.04	78	3900
9	0.05	L3	0.1	85	1700
10	0.01	L4	0.02	<1	—
11	0.02	L4	0.04	<1	—
12	0.05	L4	0.1	<5	—

Entry^a	x	Ligand	y	Yield^b/%	TON^c
1	0.01	L1	0.02	<5	—
2	0.02	L1	0.04	77	3850
3	0.05	L1	0.1	78	1560
4	0.01	L2	0.02	62	6200
5	0.02	L2	0.04	85	4250
6	0.05	L2	0.1	89	1780
7	0.01	L3	0.02	<5	—
8	0.02	L3	0.04	47	2350
9	0.05	L3	0.1	94	1880
10	0.01	L4	0.02	<1	—
11	0.02	L4	0.04	<1	—
12	0.05	L4	0.1	<5	—

Entry^a	x	Ligand	y	Yield^b/%	TON^c
1	0.01	L1	0.02	<5	—
2	0.02	L1	0.04	77	3850
3	0.05	L1	0.1	78	1560
4	0.01	L2	0.02	62	6200
5	0.02	L2	0.04	85	4250
6	0.05	L2	0.1	89	1780
7	0.01	L3	0.02	<5	—
8	0.02	L3	0.04	47	2350
9	0.05	L3	0.1	94	1880
10	0.01	L4	0.02	<1	—
11	0.02	L4	0.04	<1	—
12	0.05	L4	0.1	<5	—

3-芳基茚基膦配体的合成及其在低催化剂用量下Suzuki-Miyaura交叉偶联反应中的应用

Synthesis and Application of 3-Aryl Substituted Indenyl Phosphines in Suzuki-Miyaura Cross-Coupling Reactions at Low Catalyst Loadings

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 4

References 19

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Dongting Cheng, Nengbo Zhu, Hongli Bao. Recent Advances in the Double Hydrophosphination and Hydrophosphinylation of Alkynes [J]. Chinese Journal of Organic Chemistry, 2026, 46(9): 3546-3558.
[2]	Ruinan Zhang, Qizhi Zheng, Shengyi Lai, Wenjun Luo, Bing Xu, Zhan-Ming Zhang, Junliang Zhang. Applications of Sadphos in Earth-Abundant Metal Catalysis [J]. Chinese Journal of Organic Chemistry, 2026, 46(9): 3390-3398.
[3]	Zulian Liu, Dexi Yang, Hu Fang, Weichao Xue, Haiyan Fu, Ruixiang Li, Xueli Zheng, Hua Chen. Synthesis of Phosphine Ligands via a Coordination Assembly Strategy and Their Applications in Hydroformylation [J]. Chinese Journal of Organic Chemistry, 2025, 45(8): 2960-2967.
[4]	Tianlei Ren, Xin Wang, Huan Cong. Anthracene Photodimer-Derived Chiral Monophosphine Ligands: Preparative Route through Chemical Resolution and Synthetic Application in Asymmetric Allylic Amination [J]. Chinese Journal of Organic Chemistry, 2025, 45(6): 2208-2221.
[5]	Cheng Luo, Yanli Yin, Zhiyong Jiang. Recent Advances in Asymmetric Synthesis of P-Chiral Phosphine Oxides [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 1963-1976.
[6]	Lei Zhang, Chen Yang, Xuefeng Guo, Fanyang Mo. Research Progress of Suzuki-Miyaura Cross-Coupling Reaction Mechanism [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3492-3510.
[7]	Zheng Kanghe, Zhou Bingwei, Jin Hongwei, Liu Yunkui. Bifunctional Phosphine Ligand-Enabled Gold(I)-Catalyzed Efficient Synthesis of 1,5-Benzodiazepines [J]. Chinese Journal of Organic Chemistry, 2020, 40(8): 2520-2525.
[8]	Liu Yuanhua, Dong Xiu-Qin, Zhang Xumu. Recent Advances of Nickel-Catalyzed Homogeneous Asymmetric Hydrogenation [J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1096-1104.
[9]	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.
[10]	Li Shuailong, Li Zhuangxing, You Cai, Lü Hui, Zhang Xumu. Recent Advances in Asymmetric Hydroformylation [J]. Chin. J. Org. Chem., 2019, 39(6): 1568-1582.
[11]	Wu Fang, Zhang Wenjing, An Dongli, Li Yanyun, Gao Jingxing. Asymmetric Transfer Hydrogenation of Ketones Catalyzed by Chiral Multidentate Aminophosphine Ligands/Iron Cluster [J]. Chin. J. Org. Chem., 2017, 37(5): 1295-1299.
[12]	Chen Yong, Meng Jiben. Synthesis and Properties of Novel Photomodulation Magnetic Molecular-Based Magnet Based on Photochromic Biindenylidenedione Derivative [J]. Chin. J. Org. Chem., 2016, 36(8): 1869-1877.
[13]	Zhao Wenxian, Yang Daiyue, Zhang Yuhua. Progress in Efficient Chiral Phosphine Ligand [J]. Chin. J. Org. Chem., 2016, 36(10): 2301-2316.
[14]	Li Qinghan, Ding Yong, Zhang Gang, Zhang Zhen, Mo Song. Advance on Applications of Microwave Technique in Palladium- Catalyzed Suzuki-Miyaura Cross-Coupling Reaction [J]. Chin. J. Org. Chem., 2016, 36(1): 83-104.
[15]	Han Zhijun, Mao Shulan, Peng Hui, Pi Yunxiao, Chen You, Liu Shenghua, Yu Guangao. Synthetic and Structural Studies on Indenyl Phosphine Gold Complexes and Application as Catalyst for Hydration of Alkynes [J]. Chin. J. Org. Chem., 2014, 34(5): 893-897.