Metal-Free Cascade Isocyanide Phosphorylation/Cyclization to Synthesize 2-Phosphinoylindoles

doi:10.6023/cjoc202503002

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (10): 3856-3865.DOI: 10.6023/cjoc202503002 Previous Articles Next Articles

ARTICLES

无金属下异腈的膦酰化串联环化反应合成2-膦酰基吲哚

曹锐锋^a^,^†, 肖蔺^a^,^†, 龙天宇^a^,^b^,^†, 古家侗^a, 李杨华^c, 孔晗晗^a^,^*(), 阳青青^a, 黄年玉^d, 王龙^a^,^e^,^*()

^a 三峡大学材料与化工学院无机非金属晶态与能源转换材料重点实验室湖北宜昌 443002
^b 三峡大学水利与环境学院湖北宜昌 443002
^c 湖北普瑞提化工科技有限公司湖北宜昌 443200
^d 三峡大学生物与制药学院天然产物研究与利用湖北省重点实验室湖北宜昌 443002
^e 湖北三峡实验室湖北宜昌 443007

收稿日期:2025-03-03 修回日期:2025-04-27 发布日期:2025-05-20
作者简介:
^† 共同第一作者.
基金资助:
国家自然科学基金(22301160); 国家自然科学基金(21702121); 国家自然科学基金(21602123); 高等学校学科创新引智计划(111计划); 高等学校学科创新引智计划(D20015); 湖北省自然科学基金(2025AFA116); 湖北省自然科学基金(2025AFD270); 湖北省自然科学基金(2023AFB026); 中国博士后科学基金(2023M742043); 湖北三峡实验室基金(SC240014); 湖北三峡实验室基金(SC232008); 湖北三峡实验室基金(SC213008); 及天然产物研究与利用湖北省重点实验室基金(2024NPRD08); 及天然产物研究与利用湖北省重点实验室基金(2022NPRD04)

Metal-Free Cascade Isocyanide Phosphorylation/Cyclization to Synthesize 2-Phosphinoylindoles

Ruifeng Cao^a, Lin Xiao^a, Tianyu Long^a^,^b, Jiadong Gu^a, Yanghua Li^c, Han-Han Kong^a^,^*(), Qing-Qing Yang^a, Nianyu Huang^d, Long Wang^a^,^e^,^*()

^a Key Laboratory of Inorganic Nonmetallic Crystalline and Energy Conversion Materials, College of Materials and Chemical Engineering, China Three Gorges University, Yichang, Hubei 443002
^b College of Hydraulic and Environmental Engineering, China Three Gorges University, Yichang, Hubei 443002
^c Hubei Pretty Chemical Technology Co., Ltd., Yichang, Hubei 443200
^d Hubei Key Laboratory of Natural Products Research and Development, College of Biological and Pharmaceutical Science, China Three Gorges University, Yichang, Hubei 443002
^e Hubei Three Gorges Laboratory, Yichang, Hubei 443007

Received:2025-03-03 Revised:2025-04-27 Published:2025-05-20
Contact: * konghanhan@ctgu.edu.cn; wanglongchem@ctgu.edu.cn
About author:
^† These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(22301160); National Natural Science Foundation of China(21702121); National Natural Science Foundation of China(21602123); Programme of Introducing Talents of Discipline to Universities (111 Project(D20015); Natural Science Foundation of Hubei Province(2025AFA116); Natural Science Foundation of Hubei Province(2025AFD270); Natural Science Foundation of Hubei Province(2023AFB026); China Postdoctoral Science Foundation(2023M742043); Hubei Three Gorges Laboratory Foundation(SC240014); Hubei Three Gorges Laboratory Foundation(SC232008); Hubei Three Gorges Laboratory Foundation(SC213008); Foundation of Hubei Key Laboratory of Natural Products Research and Development(2024NPRD08); Foundation of Hubei Key Laboratory of Natural Products Research and Development(2022NPRD04)

1. .pdf(7014KB)

Abstract

A novel approach for the efficient synthesis of 2-phosphinoylindoles has been devised through P-centered anion nucleophilic addition to 2-isocyanobenzaldehydes, followed by cascade cyclization. This method uniquely employs base- promoted activation without requiring metals, light, or electrical energy, thereby offering a metal-free strategy for constructing phosphine-functionalized indoles.

Key words: metal-free, 2-phosphinoylindole, 2-isocyanobenzaldehyde, P-centered anion, nucleophilic addition

Cite this article

Ruifeng Cao, Lin Xiao, Tianyu Long, Jiadong Gu, Yanghua Li, Han-Han Kong, Qing-Qing Yang, Nianyu Huang, Long Wang. Metal-Free Cascade Isocyanide Phosphorylation/Cyclization to Synthesize 2-Phosphinoylindoles[J]. Chinese Journal of Organic Chemistry, 2025, 45(10): 3856-3865.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 8

Figure 1. Representative biologically active compounds and ligands containing phosphinoylindoles skeleton

Scheme 1. Previous reports on the synthesis of 2-phosphinoyl indoles and our work

Entry	Base	Solvent	Yield^b/%
1	DBU	CH₂Cl₂	55
2	DBU	DMSO	67
3	DBU	Toluene	31
4	DBU	MeCN	73
5	DABCO	MeCN	N.D.
6	TMG	MeCN	69
7	t-BuOK	MeCN	51
8	Na₂CO₃	MeCN	N.D.
9^c	DBU	MeCN	76
10^c^,^d	DBU	MeCN	N.D.
11^c^,^e	DBU	MeCN	85
12^c^,^f	DBU	MeCN	74
13^c^,^e^,^g	DBU	MeCN	84 (87)^h

Table 1. Optimization of the reaction conditionsa

Table 2. Substrate scope of 2-phosphonyl indolesa,b

Scheme 2. Gram-scale synthesis and synthetic transformations

Entry	Variation of reaction condition	Yield^b/%
1	—	87
2	w/o base	0
3	TEMPO (5.0 equiv.)	84
4	BHT (5.0 equiv.)	82

Table 3. Control experimenta

Scheme 3. Mechanism experiment

Scheme 4. Plausible reaction mechanism

References 16

[1]	(a) Chen, L.; Liu, X. Y.; Zou, Y. X. Adv. Synth. Catal. 2020, 362, 1724.
	(b) Li, C.; Wang, J.; Yang, S. D. Chem. Commun. 2021, 57, 7997.
	(c) Zhu, P. W.; Ma, H. M.; Li, Y.; Miao, L. Z.; Zhu, J. J. Org. Chem. 2023, 88, 2069.
[2]	(a) Steininger, H.; Schuster, M.; Kreuer, K. D.; Kaltbeitzel, A.; Bingöl, B.; Meyer, W. H.; Schauff, S.; Brunklaus, G.; Maier, J.; Spiess, H. W. Phys. Chem. Chem. Phys. 2007, 9, 1764. doi: 10.1039/b618686f pmid: 20349973
	(b) Kirumakki, S.; Huang, J.; Subbiah, A.; Yao, J.; Rowland, A.; Smith, B.; Mukherjee, A.; Samarajeewa, S.; Clearfield, A. J. Mater. Chem. 2009, 19, 2593. pmid: 20349973
	(c) Spampinato, V.; Tuccitto, N.; Quici, S.; Calabrese, V.; Marletta, G.; Torrisi, A.; Licciardello, A. Langmuir 2010, 26, 8400. doi: 10.1021/la9048314 pmid: 20349973
	(d) Joly, D.; Bouit, P. A.; Hissler, M. J. Mater. Chem. 2016, 4, 3686. pmid: 20349973
[3]	(a) Dang, Q.; Liu, Y.; Cashion, D. K.; Kasibhatla, S. R.; Jiang, T.; Taplin, F.; Jacintho, J. D.; Li, H; Sun, Z.; Fan, Y.; DaRe, J.; Tian, F.; Li, W.; Gibson, T.; Lemus, R.; Poelje, P. D.; Potter, S. C.; Erion, M. D. J. Med. Chem. 2011, 54, 153. doi: 10.1021/jm101035x pmid: 21126019
	(b) Chen, X.; Kopecky, D. J.; Mihalic, J.; Jeffries, S.; Min, X.; Heath, J.; Deignan, J.; Lai, S. J.; Fu, Z.; Guimaraes, C.; Shen, S.; Li, S.; Johnstone, S.; Thibault, S.; Xu, H.; Cardozo, M.; Shen, W.; Walker, N.; Kayser, F.; Wang, Z. J. Med. Chem. 2012, 55, 3837. pmid: 21126019
[4]	Budnikova, Y. H.; Sinyashin, O. G. D. Russ. Chem. Rev. 2015, 84, 917.
[5]	(a) Rataboul, F.; Zapf, A.; Jackstell, R.; Harkal, S.; Riermeier, T.; Monsees, A.; Dingerdissen, U.; Beller, M. Chem.-Eur. J. 2004, 10, 2983. pmid: 15214081
	(b) Lee, H. W.; Lam, F. L.; So, C. M.; Lau, C. P.; Chan, A. S. C.; Kwong, F. Y. Angew. Chem., Int. Ed. 2009, 48, 7436. pmid: 15214081
	(c) Regina, G. L.; Coluccia, A.; Silvestri, R. Antiviral Chem. Chemother. 2010, 20, 213. pmid: 15214081
	(d) Alexandre, F. R.; Amador, A.; Bot, S.; Caillet, C.; Convard, T.; Jakubik, J.; Musiu, C.; Poddesu, B.; Vargiu, L.; Liuzzi, M.; Roland, A.; Seifer, M.; Standring, D.; Storer, R.; Dousson, C. B. J. Med. Chem. 2011, 54, 392. pmid: 15214081
	(e) Cai, B. G.; Xuan, J.; Xiao, W. J. Sci. Bull. 2019, 64, 337. pmid: 15214081
	(f) Chen, Z. H.; Li, T. Z.; Wang, N. Y.; Ma, X. F.; Ni, S. F.; Zhang, Y. C.; Shi, F. Angew. Chem., Int. Ed. 2023,62, e20230049. pmid: 15214081
[6]	(a) Sun, W. B.; Xue, J. F.; Zhang, G. Y.; Zeng, R. S.; An, L. T.; Zhang, P. Z.; Zou, J. P. Adv. Synth. Catal. 2016, 358, 1753.
	(b) Wang, L.; Wu, Y.; Liu, Y.; Yang, H.; Liu, X.; Wang, J.; Li, X.; Jiang, J. Org. Lett. 2017, 19, 782.
	(c) Chen, L.; Zou, Y. X. Org. Biomol. Chem. 2018, 16, 7544.
	(d) Hu, C.; Hong, G.; He, Y.; Zhou, C.; Kozlowski, M. C.; Wang, L. J. Org. Chem. 2018, 83, 4739.
	(e) Zou, Y. X.; Liu, X. Y.; Zhang, J.; Yang, H. L.; Yang, X. Y.; Liu, X. L.; Chu, Y. W.; Chen, L. Adv. Synth. Catal. 2019, 361, 5311.
[7]	(a) Kondoh, A.; Yorimitsu, H.; Oshima, K. Org. Lett. 2010, 12, 1476. doi: 10.1021/ol1001544 pmid: 20205465
	(b) Gao, Y.; Lu, G.; Zhang, P.; Zhang, L.; Tang, G.; Zhao, Y. Org. Lett. 2016, 18, 1242. pmid: 20205465
	(c) Wang, H.; Li, S.; Wang, B.; Li, B. Org. Chem. Front. 2018, 5, 88. pmid: 20205465
	(d) Chen, C.; Ding, J.; Liu, L.; Huang, Y.; Zhu, B. Adv. Synth. Catal. 2022, 364, 200. pmid: 20205465
[8]	(a) Wang, H.; Li, X.; Wu, F.; Wan, B. Synthesis 2012, 44, 941.
	(b) Shaikh, R. S.; Ghosh, I.; König, B. Chem.-Eur. J. 2017, 23, 12120.
	(c) Ren, Z. L.; Kong, H. H.; Lu, W. T.; Sun, M.; Ding, M. W. Tetrahedron 2018, 74, 184.
	(d) Chen, L.; Zhou, Y. X.; Fang, X. Y.; Wu, J.; Sun, X. H. Org. Biomol. Chem. 2018, 16, 7417.
	(e) Pan, J.; Zhao, R.; Guo, J.; Ma, D.; Xia, Y.; Gao, Y.; Xu, P.; Zhao, Y. Green Chem. 2019, 21, 792.
	(f) Zou, Y. X.; Liu, X. Y.; Zhang, J.; Yang, H. L.; Yang, X. Y.; Liu, X. L.; Chu, Y. W.; Chen, L. Adv. Synth. Catal. 2019, 361, 5311.
	(g) Lu, G.; Huangfu, X.; Wu, Z. A.; Tang, G.; Zhao, Y. Adv. Synth. Catal. 2019, 361, 4961.
	(h) An, D.; Sang, J.; Hu, R.; Chen, J.; Feng, L.; Rao, W. Adv. Synth. Catal. 2021, 363, 3496.
	(i) Shao, A.; Chen, J.; Wang, L.; Yi, M.; Yang, H.; Zhang, Y.; Fan, S.; Chen, S.; Wu, H.; Shi, R. Org. Chem. Front. 2022, 9, 4379.
	(j) Mo, K.; Zhou, X.; Wang, J.; Wu, J.; Zhao, Y. Org. Lett. 2023, 25, 3956.
	(k) Zhou, X.; Wang, J.; Shen, Y.; Ma, D.; Zhao, Y.; Wu, J. J. Org. Chem. 2023, 88, 17521.
	(l) Pan, Y. Y.; Zhu, X. W.; Shi, L.; Jiang, G.; Wu, X. X. J. Org. Chem. 2023, 88, 9843.
	(m) Sun, J.; Ye, H.; Fei, S.; Pan, Y. Y.; Zhu, X. W.; Wu, X. X. Org. Lett. 2023, 25, 5220.
	(n) Zhang, Z.; Liu, M.; Liu, M.; Pan, C.; Mao, Z.; Zhang, X. J. Org. Chem. 2024, 89, 2996.
	(q) Wang, J.; Zhang, Z.; Shen, Y.; Zhao, Y.; Wu, J. Org. Lett. 2024, 26, 4700.
	(p) Zhou, X.; Wang, J.; Ma, D.; Shen, Y.; Zhao, Y.; Wu, J. Chem. Commun. 2024, 60, 7351.
	(q) Banu, S.; Kumari, S.; Roy, S.; Kundu, S. J. Catal. 2024, 438, 115710.
	(t) Zeng, F. L.; Jia, Z.; Loh, T. P. Adv. Synth. Catal. 2024, 366, 4536.
[9]	(a) Gulevich, A. V.; Zhdanko, A. G.; Orru, R. V. A.; Nenajdenko, V. G. Chem. Rev. 2010, 110, 5235. doi: 10.1021/cr900411f pmid: 37029692
	(b) Zhang, B.; Mück-Lichtenfeld, C.; Daniliuc, C. G.; Studer, A. Angew. Chem., Int. Ed. 2013, 52, 10792. pmid: 37029692
	(c) Zhang, B.; Studer, A. Chem. Soc. Rev. 2015, 44, 3505. doi: 10.1039/c5cs00083a pmid: 37029692
	(d) Yuan, Y. C.; Liu, H. L.; Hu, X. B.; Wei, Y.; Shi, M. Chem.-Eur. J. 2016, 22, 13059. doi: 10.1002/chem.201602920 pmid: 37029692
	(e) Hu, Z.; Yuan, H.; Men, Y.; Liu, Q.; Zhang, J.; Xu, X. Angew. Chem., Int. Ed. 2016. 128, 7193. pmid: 37029692
	(f) Giustiniano, M.; Basso, A.; Mercalli, V.; Massarotti, A.; Novellino, E.; Tron, G. C.; Zhu, J. Chem. Soc. Rev. 2017, 46, 1295. pmid: 37029692
	(g) Hu, Z.; Dong, J.; Yang, M.; Li, Y.; Xu, X. Chem. Commun. 2017, 53, 1739. pmid: 37029692
	(h) Bao, L.; Liu, J.; Xu, L.; Hu, Z.; Xu, X. Adv. Synth. Catal. 2018. 360, 1870. pmid: 37029692
	(i) Yang, W. C.; Wei, K.; Sun, X.; Zhu, J.; Wu, L. Org. Lett. 2018, 20, 3144. pmid: 37029692
	(j) Liu, Y.; Li, S. J.; Chen, X. L.; Fan, L. L.; Li, X. Y.; Zhu, S. S.; Qu, L. B.; Yu, B. Adv. Synth. Catal. 2020, 362, 688. pmid: 37029692
	(k) Zhang, T.; Yu, M.; Huang, H. Chem. Sci. 2021, 12, 10501. pmid: 37029692
	(l) Dong, J.; Wang, L.; Li, H.; Leng, X.; Guo, X.; Hu, Z.; Xu, X. Org. Chem. Front. 2021, 8, 2595. pmid: 37029692
	(m) Puig, J.; Bonjoch, J.; Bradshaw, B. Org. Lett. 2023, 25, 6539. pmid: 37029692
	(n) Drennhaus, T.; Leifert, D.; Lammert, J.; Drennhaus, J. P.; Bergander, K.; Daniliuc, C. G.; Studer, A. J. Am. Chem. Soc. 2023, 145, 8665. doi: 10.1021/jacs.3c01667 pmid: 37029692
	(o) Li, J.; Zhao, Z. W.; Zheng, S.; He, P.; Qiu, J. Y.; Zhou, Q. Q.; Ren, Z. L. Org. Chem. Front. 2023, 10, 3252. pmid: 37029692
	(p) Zheng, S.; Fan, H. J.; Liu, S. S.; Xu, Y.; Zhao, Z. W.; Kong, H. H.; He, P.; Wang, L.; Ren, Z. L. Org. Chem. Front. 2024, 11, 1775. pmid: 37029692
	(q) Liu, H.; Guo, M.; Jia, M.; Zhang, J.; Xu, X. Org. Lett. 2025, 27, 778. pmid: 37029692
[10]	(a) Gao, Y.; Wu, J.; Xu, J.; Wang, X.; Tang, G.; Zhao, Y. Asian. J. Org. Chem. 2014, 3, 691. pmid: 27934489
	(b) Zhang, B.; Daniliuc, C. G.; Studer, A. Org. Lett. 2014, 16, 250. doi: 10.1021/ol403256e pmid: 27934489
	(c) Li, Y.; Qiu, G.; Y. S.; Ding, Q.; Wu, J. Tetrahedron 2014, 70, 4652. pmid: 27934489
	(d) Noël-Duchesneau, L.; Lagadic, E.; Morlet-Savary, F.; Lohier, J. F.; Chataigner, I.; Breugst, M.; Lalevee, J.; Gaumont, A. C.; Lakhdar, S. Org. Lett. 2016, 18, 5900. pmid: 27934489
	(e) Li, C. X.; Tu, D. S.; Yao, R.; Yan, H.; Lu, C. S. Org. Lett. 2016, 18, 4928. pmid: 27934489
	(f) Li, D.; Mao, T.; Huang, J.; Zhu, Q. Org. Lett. 2017, 19, 3223. pmid: 27934489
	(g) Wang, C. H.; Li, Y. H.; Yang, S. D. Org. Lett. 2018, 20, 2382. pmid: 27934489
	(h) Liu, Y.; Chen, X. L.; Zeng, F. L.; Sun, K.; Qu, C.; Fan, L. L.; An, Z. L.; Li, R.; Jing, C. F.; Wei, S. K.; Qu, L.B. J. Org. Chem. 2018, 83, 11727. pmid: 27934489
	(i) Yang, W.; Li, B.; Zhang, M.; Wang, S.; Ji, Y.; Dong, S.; Feng, J.; Yuan, S. Chin. Chem. Lett. 2020, 31, 1313. pmid: 27934489
	(j) Liu, Y.; Chen, X. L.; Li, X. Y.; Zhu, S. S.; Li, S. J.; Song, Y.; Qu, L. B.; Yu, B. J. Am. Chem. Soc. 2021, 143, 964. pmid: 27934489
	(k) Yu, J. X.; Cheng, Y. Y.; Chen, B.; Tung, C. H.; Wu, L. Z. Angew. Chem., Int. Ed. 2022,61, e202209293. pmid: 27934489
	(l) Ma, C.; Li, X.; Chen, X.; He, X.; Zhang, S. T.; Jiang, Y. Q.; Yu, B. Org. Lett. 2023, 25, 8016. pmid: 27934489
	(m) Banjare, S. K.; Lezius, L.; Horst, E. S.; Leifert, D.; Daniliuc, C. G.; Alasmary, F. A.; Studer, A. Angew. Chem., Int. Ed. 2024,63, e202404275. pmid: 27934489
	(n) Zhang, X.; Wang, P.; Jiang, Y.; Yang, B.; Xiao, T. J. Org. Chem. 2025, 90, 1262. pmid: 27934489
[11]	Liu, Y.; Jia, M.; Wang, G.; Yang, W.; Xu, X. Chem. Commun. 2024, 60, 7196.
[12]	(a) Liu, N.; Chao, F.; Liu, M. G.; Huang, N. Y.; Zou, K.; Wang, L. J. Org. Chem. 2019, 84, 2366. doi: 10.1021/acs.joc.8b03242 pmid: 30676019
	(b) Liu, J.; Liu, N.; Yang, Q.; Wang, L. Org. Chem. Front. 2021, 8, 5296. pmid: 30676019
	(c) Liu, J.; Xie, Y.; Yang, Q.; Huang, N.; Wang, L. Chin. J. Org. Chem. 2021, 41, 2374 (in Chinese). pmid: 30676019
	(刘金妮, 谢益碧, 阳青青, 黄年玉, 王龙, 有机化学, 2021, 41, 2374.) pmid: 30676019
	(d) Luo, X.; Xie, Y.; Huang, N.; Wang, L. Chin. J. Org. Chem. 2022, 42, 838 (in Chinese). pmid: 30676019
	(罗享豪, 谢益碧, 黄年玉, 王龙, 有机化学, 2022, 42, 838.) pmid: 30676019
	(e) Ma, Y. H.; He, X. Y.; Wang, L.; Yang, Q. Q. J. Org. Chem. 2022, 87, 11852. pmid: 30676019
	(f) Luo, X.; Tian, A.; Pei, M.; Yan, J.; Liu, X.; Wang, L. Chem.-Eur. J. 2022,28, e202103361. pmid: 30676019
	(g) Liu, J.; Li, Y.; Liu, N.; Huang, N.; Wang, L.; Li, D. Org. Chem. Front. 2022, 9, 6179. pmid: 30676019
	(h) Kong, H. H.; Zhu, C.; Deng, S.; Xu, G.; Zhao, R.; Yao, C.; Xiang, H. M.; Zhao, C.; Qi, X.; Xu, H. J. Am. Chem. Soc. 2022, 144, 21347. pmid: 30676019
	(i) Hua, T. B.; Ma, Y. H.; He, X. Y.; Wang, L.; Yan, J. Y.; Yang, Q. Q. Org. Chem. Front. 2022, 9, 3558. pmid: 30676019
	(j) Yan, C. Y.; Wu, Z. W.; He, X. Y.; Ma, Y. H.; Peng, X. R.; Wang, L.; Yang, Q. Q. J. Org. Chem. 2023, 88, 647. pmid: 30676019
	(k) Pei, M.; Tian, A.; Yang, Q.; Huang, N.; Wang, L.; Li, D. Green Synth. Catal. 2023, 4, 135. pmid: 30676019
	(l) Li, M.; Mei, S.; Zheng, Y.; Wang, L.; Ye, L. Chem. Commun. 2023, 59, 13478. pmid: 30676019
	(m) Chen, N.; Long, T.; Kong, H. H.; Wu, Z. W.; Yang, Q. Q.; Huang, N.; Wang, L. Org. Chem. Front. 2024, 11, 2780. pmid: 30676019
	(n) Wu, Z. W.; Kong, H. H.; Wei, Y.; Zhou, W. C.; Wang, L.; Lu, L. Q.; Yang, Q. Q. Green Synth. Catal. 2024, 6, 187. pmid: 30676019
[13]	Liu, Y.; Xie, P.; Li, J.; Bai, W. J.; Jiang, J. Org. Lett. 2019, 21, 4944.
[14]	Turnu, F.; Luridiana, A.; Cocco, A.; Porcu, S.; Frongia, A.; Sarais, G.; Secci, F. Org. Lett. 2019, 21, 7329.
[15]	(a) Hirai, T.; Han, L. B. J. Am. Chem. Soc. 2006, 128, 7422.
	(b) Yuan, Q.; Liu, H. W.; Cai, Z. J.; Ji, S. J. ACS Omega 2021, 6, 8495.
[16]	(a) Kobayashi, S.; Kiyohara, H.; Nakamura, Y.; Matsubara, R. J. Am. Chem. Soc. 2004, 126, 6558. pmid: 32097020
	(b) Kondoh, A.; Ishikawa, S.; Aoki, T.; Terada, M. Chem. Commun. 2016, 52, 12513. pmid: 32097020
	(c) Kondoh, A.; Ozawa, R.; Aoki, T.; Terada, M. Org. Biomol. Chem. 2017, 15, 7277. doi: 10.1039/c7ob02059g pmid: 32097020
	(d) Kondoh, A.; Aoki, T.; Terada, M. Chem.-Eur. J. 2018, 24, 13110. doi: 10.1002/chem.201803218 pmid: 32097020
	(e) Kondoh, A.; Aita, K.; Ishikawa, S.; Terada, M. Org. Lett. 2020, 22, 2105. doi: 10.1021/acs.orglett.0c00619 pmid: 32097020

无金属下异腈的膦酰化串联环化反应合成2-膦酰基吲哚

Metal-Free Cascade Isocyanide Phosphorylation/Cyclization to Synthesize 2-Phosphinoylindoles

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 8

References 16

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Yuhan Zhao, Huimin Ma, Shulin Ge, Lingbin Kong. Iodine-Catalyzed Intermolecular Cyclopropanation of Olefins with Active Methylene Compounds [J]. Chinese Journal of Organic Chemistry, 2025, 45(9): 3469-3477.
[2]	Lianji Zhang, Bingfu Wang, Dalong Pan, Cuiping Wang, Yuhui Zhao, Haijun Chi, Yan Dong, Wanguo Wei, Zhiqiang Zhang. Acetic Acid-Mediated Metal-Free Oxidative C—H Cross-Coupling of Imidazopyridines and Glyoxal Hydrates [J]. Chinese Journal of Organic Chemistry, 2025, 45(8): 2923-2931.
[3]	Haojie Ma, Fengyuan Zhou, Yumeng He, Xiaoqiang Zhou, Zhou Sun, Yuqi Zhang. Iodine-Promoted Intermolecular Cyclization for the Synthesis of 2-Phenylquinazolines [J]. Chinese Journal of Organic Chemistry, 2025, 45(6): 2157-2162.
[4]	Mengqin Liu, Yiting Chen, Juyuan Zhang, Heye Zhou, Tao Qin, Bin Liu. Efficient Synthesis of Diaryl Sulfides via Three Component Cross Coupling [J]. Chinese Journal of Organic Chemistry, 2025, 45(4): 1283-1296.
[5]	Zheng Wang, Yuqin Lan, Zhiyi Zhou, Yingzi Tan, Zongcheng Wang. Selenium Mediated Cyclization Reaction of Isonitriles with o-Aminophenols to Synthesize 2-Aminobenzoxazoles [J]. Chinese Journal of Organic Chemistry, 2025, 45(4): 1379-1385.
[6]	Guiling Xie, Sudhakar Reddy Mopuri, Jie Li, Yuanyong Yang, Tie-Gen Chen. One-Pot Transition-Metal-Free Synthesis of Carboline Derivatives via Dual C—N Bond Formation [J]. Chinese Journal of Organic Chemistry, 2025, 45(10): 3824-3837.
[7]	Yanmei Yan, Hongli Zhang, Min Yuan, Ruijia Qin, Zhenxing Ren, Yingchun He. One-Pot Metal-Free Synthesis of New 1,2,3-Triazolobenzodiaze-pinones by a Sequential Ugi 4CR/Alkyne-Azide Cycloaddition Reaction [J]. Chinese Journal of Organic Chemistry, 2025, 45(10): 3923-3931.
[8]	Zhenru Huang, Guoshun Jin, Tianyu Chen, Bin Feng, Xinkang Shi, Minfang Chen, Lusheng Hua, Qing Xu. Efficient Construction of Quinoxaline Derivatives by Cesium Hydroxide-Catalyzed Mild Aerobic Annulation Reaction [J]. Chinese Journal of Organic Chemistry, 2024, 44(9): 2933-2942.
[9]	Yushen Gao, Yuanyuan Gao, An'an Zhang, Lu Li, Weizhi Geng, Fenghua Zhang, Fei Li, Lantao Liu. BF₃•OEt₂ Mediated Intramolecular Cyclization of 2-Alkynylanilines Approach to 3-Sulfenylindoles [J]. Chinese Journal of Organic Chemistry, 2024, 44(9): 2785-2795.
[10]	Shulin Zhang, Zhou Zhang, Meng Sun. Ag(I)-Catalyzed Addition of Cyclopropenones and Alcohols via C—C Bond Cleavage [J]. Chinese Journal of Organic Chemistry, 2024, 44(7): 2233-2240.
[11]	Rou Ding, Siyu Shi, Chao Ma, Wei Wei, Yufen Lü. Metal-Free 1,8-Diazabicyclo(5.4.0)-undec-7-ene Mediated Synthesis of α-Acetal Amides through Reaction of Glyoxylic Acid Acetalde with Aryl Isothiocyanates [J]. Chinese Journal of Organic Chemistry, 2024, 44(7): 2216-2222.
[12]	Yongsheng Tian, Lanfeng Wei, Jiawei Huang, Yu Wei, Liang Xu, Shuai Liu. Deboronative Selenylation, Bromination, or Hydroxylation of Organic Boronic Acids Facilitated by Tetrabutylammonium Tribromide under Transition Metal-Free Conditions [J]. Chinese Journal of Organic Chemistry, 2024, 44(6): 1987-1997.
[13]	Guodong Ju, Guangyu Zhou, Yingsheng Zhao. Transition-Metal-Free Regioselective Thiocyanation of Triisopropylsilane (TIPS)-Protected Phenols [J]. Chinese Journal of Organic Chemistry, 2024, 44(4): 1327-1336.
[14]	Yunhui Wan, Fumei Yang, Minghan Chen, Deli Sun, Danfeng Ye. Esterification of N-Benzyl-N-t-butoxycarbonyl-amides and Unsaturated Alcohol under Transition Metal-Free Conditions [J]. Chinese Journal of Organic Chemistry, 2024, 44(4): 1293-1300.
[15]	Jie Liu, Feng Han, Shuangyan Li, Tianyu Chen, Jianhui Chen, Qing Xu. Transition Metal-Free Selective Aerobic Olefination of Methyl N-Heteroarenes with Alcohols [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 573-583.