Electrochemical Enabled Phosphorylation of α-Diazoester to Access Phosphinic Hydrazone

doi:10.6023/cjoc202309022

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (3): 1013-1020.DOI: 10.6023/cjoc202309022 Previous Articles Next Articles

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电化学促使α-重氮酯的磷酸化构筑亚膦酸腙

孙雪, 颜廷涛, 闫克鲁, 杨建静^*(), 文江伟^*()

曲阜师范大学化学与化工学院山东省高校绿色天然产物与医药中间体重点实验室山东曲阜 273165

收稿日期:2023-09-21 修回日期:2023-11-13 发布日期:2024-04-02
作者简介:†共同第一作者
基金资助:
国家自然科学基金(21902083); 山东省自然科学基金(ZR2020QB130); 曲阜师范大学人才启动基金(6132); 曲阜师范大学人才启动基金(6125)

Electrochemical Enabled Phosphorylation of α-Diazoester to Access Phosphinic Hydrazone

Xue Sun, Tingtao Yan, Kelu Yan, Jianjing Yang(), Jiangwei Wen()

Key Laboratory of Green Natural Products and Pharmaceutical Intermediates in Colleges and Universities of Shandong Province, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, Shandong 273165

Received:2023-09-21 Revised:2023-11-13 Published:2024-04-02
Contact: *E-mail: wenjy@qfnu.edu.cn; jjyang@whu.edu.cn
About author:†The authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(21902083); Natural Science Foundation of Shandong Province(ZR2020QB130); Talent Program Foundation of Qufu Normal University(6132); Talent Program Foundation of Qufu Normal University(6125)

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Abstract

The phosphonic hydrazone represents a rare molecular fragment with promising applications in the fields of pharmaceuticals, functional materials, ligands, and synthetic intermediates. A novel electrochemical approach is presented for the generation of Ni^2＋ ions from sacrificial anode nickel, facilitating the phosphorylation of α-diazoester to construct phosphite hydrazone. The reaction was performed in an undivided cell in absence of precious metal catalyst and chemical redox reagent, exhibiting good substrate applicability. The mechanistic investigation has confirmed the predominant role of paired electrolysis in mediating the catalytic mechanism.

Key words: electrochemistry, sacrificial anode, phosphorylation, α-diazoester, phosphinic hydrazine

Cite this article

Xue Sun, Tingtao Yan, Kelu Yan, Jianjing Yang, Jiangwei Wen. Electrochemical Enabled Phosphorylation of α-Diazoester to Access Phosphinic Hydrazone[J]. Chinese Journal of Organic Chemistry, 2024, 44(3): 1013-1020.

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Fig. & Tab. 6

Scheme 1. Selective functionalization of α-diazoesters

Entry	Deviation from standard conditions	Yield^b/%
1	None	98
2	Without current	n.d.
3	ⁿBu₄NClO₄, ⁿBu₄NBr, ⁿBu₄NOAc, Et₄NBr, Et₄NTs instead of ⁿBu₄NBF₄	45~82
4	LiClO₄ instead of ⁿBu₄NBF₄	n.d.
5	CH₃CN as solvent	53
6	DCE as solvent	82
7	DMSO as solvent	77
8	Pt(＋)\|Ni(－)	n.d.
9	Pt(＋), or C rods (＋) instead of Ni(＋)	n.d.
10	C rods(－), or Ni(－) instead of Pt(－)	85, 90
11	3 mA, 5 h	88
12	8 mA, 2 h	85

Table 1. Optimization of reaction conditionsa

Table 2. Substrate scope of α-diazoester and diaryl phosphorus oxidesa

Scheme 2. Large-scale synthesis of 1c and transformation

Scheme 3. Study on mechanism of electrochemical phosphorylation of α-diazoester (a) Radical inhibition experiments. (b) Metal ion verification experiments. (c) Working electrode verification experiments. (d) CV experiments: Ni net (1.0 cm×1.0 cm) as the working electrode, Pt plate (1.0 cm×1.0 cm) as the counter electrode, Ag/AgCl as the reference electrode, nBu4BF4 (0.15 mmol), CH2Cl2 (10.0 mL), 1a (0.25 mmol/L), 1b (0.25 mmol/L)

Scheme 4. Possible mechanism of electrochemical enabled phosphorylation of α-diazoester

References 11

[1]	(a) Biçer E. Phosphorus, Sulfur Silicon Relat. Elem. 2021, 196, 791. doi: 10.1080/10426507.2021.1945062
	(b) Cai B.-G.; Xuan J.; Xiao W.-J. Sci. Bull. 2019, 64, 337. doi: 10.1016/j.scib.2019.02.002
[2]	(a) Audrieth L. F.; Gher R. J.; Smith W. C. J. Org. Chem. 1955, 20, 1288. doi: 10.1021/jo01126a018
	(b) Ephraim F.; Sackheim M. Ber. Dtsch. Chem. Ges. 1911, 44, 3416. doi: 10.1002/cber.v44:3
	(c) Tolkmith H.; Britton E. J. Org. Chem. 1959, 24, 705. doi: 10.1021/jo01087a608
[3]	(a) Boaz N. W.; Mackenzie E. B.; Debenham S. D.; Large S. E.; Ponasik J. A. J. Org. Chem. 2005, 70, 1872. doi: 10.1021/jo048312y pmid: 33679278
	(b) Wang D.-Y.; Huang J.-D.; Hu X.-P.; Deng J.; Yu S.-B.; Duan Z.-C.; Zheng Z. J. Org. Chem. 2008, 73, 2011. doi: 10.1021/jo702488j pmid: 33679278
	(c) Gross T.; Chou S.; Dyke A.; Dominguez B.; Groarke M.; Medlock J.; Ouellette M.; Reddy J. P.; Seger A.; Zook S.; Zanotti-Gerosa A. Tetrahedron Lett. 2012, 53, 1025. pmid: 33679278
	(d) You C.; Li S.; Li X.; Lv H.; Zhang X. ACS Catal. 2019, 9, 8529. doi: 10.1021/acscatal.9b02667 pmid: 33679278
	(e) Schlatzer T.; Breinbauer R. Adv. Synth. Catal. 2021, 363, 668. doi: 10.1002/adsc.202001278 pmid: 33679278
[4]	Select recent representative examples: a Wang, L.; Wu, Y.; Liu, Y.; Yang, H.; Liu, X.; Wang, J.; Li, X.; Jiang, J. Org. Lett. 2017, 19, 782. doi: 10.1021/acs.orglett.6b03752 pmid: 34766748
	(b) Ciszewski Ł. W.; Durka J.; Gryko D. Org. Lett. 2019, 21, 7028. doi: 10.1021/acs.orglett.9b02612 pmid: 34766748
	(c) Su Y.-L.; Liu G.-X.; Liu J.-W.; Tram L.; Qiu H.; Doyle M. P. J. Am. Chem. Soc. 2020, 142, 13846. doi: 10.1021/jacs.0c05183 pmid: 34766748
	(d) He F.; Koenigs R. M. Org. Lett. 2021, 23, 5831. doi: 10.1021/acs.orglett.1c01982 pmid: 34766748
	(e) Shou J.-Y.; Xu X.-H.; Qing F.-L. Angew. Chem., Int. Ed. 2021, 60, 15271. pmid: 34766748
	(f) Stivanin M. L.; Duarte M.; Leão L. P. M. O.; Saito F. A.; Jurberg I. D. J. Org. Chem. 2021, 86, 17528. doi: 10.1021/acs.joc.1c02411 pmid: 34766748
	(g) Wang F.; Nishimoto Y.; Yasuda M. J. Am. Chem. Soc. 2021, 143, 20616. doi: 10.1021/jacs.1c10517 pmid: 34766748
	(h) Chen R.; Ma G.; Li Y.; Zhang J.; Xia R.; Wang K.-K.; Liu L. J. Org. Chem. 2022, 87, 10990. doi: 10.1021/acs.joc.2c01262 pmid: 34766748
	(i) Lv Y.; Liu R.; Ding H.; Wei W.; Zhao X.; He L. Org. Chem. Front. 2022, 9, 3486. doi: 10.1039/D2QO00311B pmid: 34766748
	(j) Shou J.-Y.; Qing F.-L. Angew. Chem., Int. Ed. 2022, 61, e202208860. doi: 10.1002/anie.v61.39 pmid: 34766748
	(k) Sun Y.-T.; Rao X.; Xu W.; Xu M.-H. Org. Chem. Front. 2022, 9, 3467. doi: 10.1039/D2QO00164K pmid: 34766748
[5]	(a) Tolkmith H. J. Am. Chem. Soc. 1962, 84, 2097. doi: 10.1021/ja00870a020 pmid: 789882
	(b) Cates L. A.; Cho Y. M.; Smith L. K.; Williams L.; Lemke T. L. J. Med. Chem. 1976, 19, 1133. pmid: 789882
	(c) Bagrov F.; Matveeva T.; Petrukhin V. Chem. Technol. Fuels Oils 1997, 33, 41. doi: 10.1007/BF02768139 pmid: 789882
[6]	Audrieth L.; Gher JR R.; Smith W. C. J. Org. Chem. 1955, 20, 1288. doi: 10.1021/jo01126a018
[7]	(a) Jiang H.; Jin H.; Abdukader A.; Lin A.; Cheng Y.; Zhu C. Org. Biomol. Chem. 2013, 11, 3612. doi: 10.1039/c3ob40429c
	(b) Gu X.; Xie P.; Jiang J.; Wu Y.; Wang L. J. Chem. Res. 2018, 42, 63. doi: 10.3184/174751918X15177590137425
[8]	Balázs L. B.; Huang Y.; Khalikuzzaman J. B.; Li Y.; Pullarkat S. A.; Leung P.-H. J. Org. Chem. 2020, 85, 14763. doi: 10.1021/acs.joc.0c00181
[9]	Recent representative reviews: (a) Yan, M.; Kawamata, Y.; Baran, P. S. Chem. Rev. 2017, 117, 13230. doi: 10.1021/acs.chemrev.7b00397 pmid: 34060564
	(b) Jiang Y.; Xu K.; Zeng C. Chem. Rev. 2018, 118, 4485. doi: 10.1021/acs.chemrev.7b00271 pmid: 34060564
	(c) Liu Y.; Yi H.; Lei A. Chin. J. Chem. 2018, 36, 692. doi: 10.1002/cjoc.v36.8 pmid: 34060564
	(d) Wang H.; Gao X.; Lv Z.; Abdelilah T.; Lei A. Chem. Rev. 2019, 119, 6769. doi: 10.1021/acs.chemrev.9b00045 pmid: 34060564
	(e) Xiong P.; Xu H. C. Acc. Chem. Res. 2019, 52, 3339. doi: 10.1021/acs.accounts.9b00472 pmid: 34060564
	(f) Jiao K. J.; Xing Y. K.; Yang Q. L.; Qiu H.; Mei T. S. Acc. Chem. Res. 2020, 53, 300. doi: 10.1021/acs.accounts.9b00603 pmid: 34060564
	(g) Yamamoto K.; Kuriyama M.; Onomura O. Acc. Chem. Res. 2020, 53, 105. doi: 10.1021/acs.accounts.9b00513 pmid: 34060564
	(h) Novaes L. F. T.; Liu J.; Shen Y.; Lu L.; Meinhardt J. M.; Lin S. Chem. Soc. Rev. 2021, 50, 7941. doi: 10.1039/d1cs00223f pmid: 34060564
	(i) Yang J.; Qin H.; Yan K.; Cheng X.; Wen J. Adv. Synth. Catal. 2021, 363, 5407. doi: 10.1002/adsc.v363.24 pmid: 34060564
	(j) Yang J.; Ma J.; Yan K.; Tian L.; Li B.; Wen J. Adv. Synth. Catal. 2022, 364, 845. doi: 10.1002/adsc.v364.4 pmid: 34060564
	(k) Zhou H.-Y.; Tang H.-T.; He W.-M. Chin. J. Catal. 2023, 46, 4. doi: 10.1016/S1872-2067(22)64197-4 pmid: 34060564
	(l) Li Q.-Y.; Swaroop T. R.; Hou C.; Wang Z.-Q.; Pan Y. M.; Tang H.-T. Adv. Synth. Catal. 2019, 361, 1761. doi: 10.1002/adsc.v361.8 pmid: 34060564
	(m) He M.; Cheng S.; Pan Y.; Tang H. T.; Pan Y. M. Chin. J. Org. Chem. 2021, 41, 2354. (in Chinese) pmid: 34060564
	( 何慕雪, 程诗砚, 潘永周, 唐海涛, 潘英明, 有机化学, 2021, 41, 2354.) pmid: 34060564
	(n) Zheng Y.; Qian S.; Xu P.; Zheng B.; Huang S. L. Chin. J.Org. Chem. 2022, 42, 4275. (in Chinese) pmid: 34060564
	( 郑煜, 钱沈城, 徐鹏程, 郑斌南, 黄申林, 有机化学, 2022, 42, 4275.) pmid: 34060564
	(o) Xu H.; Meng X.; Zheng Y.; Luo J.; Huang S. L. Chin. J. Org. Chem. 2021, 41, 4696. (in Chinese) doi: 10.6023/cjoc202112016 pmid: 34060564
	( 徐鹤华, 孟祥太, 郑煜, 罗金岳, 黄申林, 有机化学, 2021, 41, 4696.) pmid: 34060564
[10]	Yuan Y.; Liu X.; Hu J.; Wang P.; Wang S.; Alhumade H.; Lei A. Chem. Sci. 2022, 13, 3002. doi: 10.1039/D1SC07248J
[11]	(a) Sun X.; Yang J.; Yan K.; Zhuang X.; Yu J.; Song X.; Zhang F.; Li B.; Wen J. Chem. Commun. 2022, 58, 8238. doi: 10.1039/D2CC02745C
	(b) Yang J.; Sun X.; Yan K.; Sun H.; Sun S.; Jia X.; Zhang F.; Wen J. Adv. Synth. Catal. 2022, 364, 2735. doi: 10.1002/adsc.v364.16

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电化学促使α-重氮酯的磷酸化构筑亚膦酸腙

Electrochemical Enabled Phosphorylation of α-Diazoester to Access Phosphinic Hydrazone

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Fig. & Tab. 6

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