Recent Progress in the Application of Difluoromethyl Diazomethane as Fluorine-Containing Building Block

doi:10.6023/cjoc202009055

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (4): 1275-1287.DOI: 10.6023/cjoc202009055 Previous Articles Next Articles

REVIEWS

二氟甲基重氮甲烷作为含氟砌块的应用研究进展

朱文庆^a, 许婷怡^a, 韩文勇^b^,^c^,^*()

a 西安工程大学环境与化学工程学院西安 710048
b 遵义医科大学药学院贵州省生物催化与手性药物合成重点实验室贵州遵义 563006
c 遵义医科大学基础药理教育部重点实验室暨特色民族药教育部国际合作联合实验室贵州遵义 563006

收稿日期:2020-09-28 修回日期:2020-11-02 发布日期:2020-12-01
通讯作者: 韩文勇
基金资助:
国家自然科学基金(21762054); 遵义医科大学优秀青年人才支持计划(18ZY-002)

Recent Progress in the Application of Difluoromethyl Diazomethane as Fluorine-Containing Building Block

Wenqing Zhu^a, Tingyi Xu^a, Wenyong Han^b^,^c^,^*()

a School of Environmental and Chemical Engineering, Xi?an Polytechnic University, Xi?an 710048
b Key Laboratory of Biocatalysis & Chiral Drug Synthesis of Guizhou Province, School of Pharmacy, Zunyi Medical University, Zunyi, Guizhou 563006
c Key Laboratory of Basic Pharmacology of Ministry of Education and Joint International Research Laboratory of Ethnomedicine of Ministry of Education, Zunyi Medical University, Zunyi, Guizhou 563006

Received:2020-09-28 Revised:2020-11-02 Published:2020-12-01
Contact: Wenyong Han
About author:
* Corresponding authors. E-mail: hanwy@zmu.edu.cn; hanwy@126.com
Supported by:
National Natural Science Foundation of China(21762054); Outstanding Youth Talent Support Programs from Zunyi Medical University(18ZY-002)

Difluoromethylation has achieved remarkable progress in the past two decades. In addition to the direct difluoromethylation and the stepwise difluoromethylation, chemical transformation starting from CF₂H-containing building blocks is a novel strategy to introduce difluoromethyl group into organic compounds. Compared with electrophilic-, nucleo- philic- and free radical-difluoromethylation reagents, the types of CF₂H-containing building blocks are still limited and less explored. Among them, difluoromethyl diazomethane (CF₂HCHN₂) is a new type of fluorine-containing building block developed in recent years, which has received much attention from researchers. The recent progress in the application of difluoromethyl diazomethane and its surrogates as fluorine-containing building blocks is summarized, focusing on the reaction types and related mechanisms, and the developmental direction in the future is prospected.

Key words: difluoromethyl diazomethane, difluoromethylation, fluorinated building block, pyrazole

Cite this article

Wenqing Zhu, Tingyi Xu, Wenyong Han. Recent Progress in the Application of Difluoromethyl Diazomethane as Fluorine-Containing Building Block[J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1275-1287.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 22

Figure 1. Difluoromethyl-containing drugs and bioactive molecules

Scheme 1. Preparations of CF3CHN2 (2) and CF2HCHN2 (4) as well as their properties

Scheme 2. [3+2] Cycloaddition reaction of CF2HCHN2 with electron-deficient alkynes

Scheme 3. [3+2] cycloaddition reaction of CF2HCHN2 with electron-deficient alkenes

Scheme 4. Synthesis of N-nitroso CF2H-pyrazolines with CF2HCHN2

Scheme 5. Synthesis of 4-fluoro-6-(difluoromethyl)pyridazine with CF2HCHN2

Scheme 6. Application of CF2HCHN2 in the synthesis of N-heterocyclics

Scheme 7. Unexpected three-component reaction as well as synthetic design of CF2H-containing pyrazoles

Scheme 8. Synthesis of difluoromethyl substituted isoxazole compounds with CF2HCHN2

Scheme 9. Copper-catalyzed four-component reaction for the synthesis of N-difluoroethyl imides

Figure 2. Analogues of drug molecular containing N-difluoro- ethyl imides

Scheme 10. Esterification of CF2HCHN2 with carboxylic acids

Figure 3. Difluoroethyl ester analogues of marketed drugs and natural products

Scheme 11. gem-Difunctionalization of CF2HCHN2

Scheme 12. Synthesis of CF2H-containing pyrazolines and pyra- zoles by continuous flow reaction

Scheme 13. Synthesis of difluoromethyl substituted cyclopropane by continuous flow reaction

Scheme 14. [3+2] cycloaddition reaction of CF2HCHN2 using continuous flow reactors

Scheme 15. Multi-step continuous flow synthesis of fluorinated pyrazoles and pyrazolines

Figure 4. CF2H-containing pesticides synthesized by continuous flow modules

Scheme 16. Reactions of Ph2S+CH2CF2H–OTf as the surrogate of CF2HCHN2

Scheme 17. Reactions of Ps-DFA as the surrogate of CF2HCHN2

Scheme 18. Reactions of DFHZ-Tfs as the surrogate of CF2HCHN2

References 48

[1]	(a) Gouverneur, V.; Muller, K. Fluorine in Pharmaceutical and Medicinal Chemistry: From Biophysical Aspects to Clinical Applications, Im-perial College Press, London, 2012. pmid: 31099931
	(b) Zhang, J.; Jin, C.; Zhang, Y. Chin. J. Org. Chem. 2014, 34,662. (in Chinese) pmid: 31099931
	( 张霁, 金传飞, 张英俊, 有机化学, 2014, 34,662.) doi: 10.6023/cjoc201310039 pmid: 31099931
	(c) Xing, L.; Blakemore, D.C.; Narayanan, A.; Unwalla, R.; Lovering, F.; Denny, R.A.; Zhou, H.; Bunnage, M.E. ChemMedChem 2015, 10,715. doi: 10.1002/cmdc.201402555 pmid: 31099931
	(d) Mei, H.; Han, J.; Fustero, S.; Medio-Simon, M.; Sedgwick, D.M.; Santi, C.; Ruzziconi, R.; Soloshonok, V.A. Chem.-Eur. J. 2019, 25,11797. doi: 10.1002/chem.201901840 pmid: 31099931
[2]	(a) Meanwell, N.A. J. Med. Chem. 2011, 54,2529. doi: 10.1021/jm1013693 pmid: 21413808
	(b) Zafrani, Y.; Sod-Moriah, G.; Yeffet, D.; Berliner, A.; Amir, D.; Marciano, D.; Elias, S.; Katalan, S.; Ashkenazi, N.; Madmon, M.; Gershonov, E.; Saphier, S. J. Med. Chem. 2019, 62,5628. pmid: 21413808
[3]	(a) Mori, T.; Ujihara, K.; Matsumoto, O.; Yanagi, K.; Matsuo, N. J. Fluorine Chem. 2007, 128,1174. pmid: 28929412
	(b) Thappali, S.R.; Varanasi, K.V.; Veeraraghavan, S.; Vakkalanka, S.K.; Mukkanti, K. J. Mass Spectrom. 2012, 47,1612. doi: 10.1002/jms.3103 pmid: 28929412
	(c) Giornal, F.; Pazenok, S.; Rodefeld, L.; Lui, N.; Vors, J.-P.; Leroux, F.R. J. Fluorine Chem. 2013, 152,2. pmid: 28929412
	(d) Rodriguez-Torres, M.; Glass, S.; Hill, J.; Freilich, B.; Hassman, D.; Di Bisceglie, A.M.; Taylor, J.G.; Kirby, B.J.; Dvory-Sobol, H.; Yang, J.-C.; An, D.; Stamm, L.M.; Brainard, D.M.; Kim, S.; Krefetz, D.; Smith, W.; Marbury, T.; Lawitz, E. J. Viral Hepatitis 2016, 23,614. pmid: 28929412
	(e) Lamb, Y.N. Drugs 2017, 77,1797. pmid: 28929412
	Zeng, J.; Xu, Z.; Ma, J. Chin. J. Org. Chem. 2020, 40,1105. (in Chinese) pmid: 28929412
	( 曾俊良, 许志红, 马军安, 有机化学, 2020, 40,1105.) doi: 10.6023/cjoc201912024 pmid: 28929412
[4]	For selected reviews on difluoromethylation, see: (a) Hu, J.; Zhang, W.; Wang, F. Chem. Commun. 2009,7465. pmid: 28632338
	(b) Lu, Y.; Liu, C.; Chen, Q.-Y. Curr. Org. Chem. 2015, 19,1638. pmid: 28632338
	(c) Belhomme, M.C.; Besset, T.; Poisson, T.; Pannecoucke, X. Chem. -Eur. J. 2015, 21,12836. pmid: 28632338
	(d) Ni, C.; Zhu, L.; Hu, J. Acta Chim. Sinica 2015, 73,90. (in Chinese) pmid: 28632338
	( 倪传法, 朱林桂, 胡金波, 化学学报, 2015, 73,90.) doi: 10.6023/cjoc202000056 pmid: 28632338
	(e) Xu, P.; Guo, S.; Wang, L.; Tang, P. Synlett 2015, 26,36. pmid: 28632338
	(f) Rong, J.; Ni, C.; Hu, J. Asian J. Org. Chem. 2017, 6,139. pmid: 28632338
	(g) Yerien, D.E.; Barata-Vallejo, S.; Postigo, A. Chem.-Eur. J. 2017, 23,14676. doi: 10.1002/chem.201702311 pmid: 28632338
	(h) Wang, W.; Yu, Q.; Zhang, Q.; Li, J.; Hui, F.; Yang, J.; Lü, J.; Jin, C.; Zhang, Y. Chin. J. Org. Chem. 2018, 38,1569. (in Chinese) pmid: 28632338
	( 王为强, 余秦伟, 张前, 李江伟, 惠丰, 杨建明, 吕剑, 金传飞, 张英俊, 有机化学, 2018, 38,1569.) doi: 10.6023/cjoc201801041 pmid: 28632338
	(i) Feng, Z.; Xiao, Y.-L.; Zhang, X. Acc. Chem. Res. 2018, 51,2264. pmid: 28632338
	(j) Mykhailiuk, P.K.; Koenigs, R.M. Chem. -Eur. J. 2019, 25,6053. pmid: 28632338
[5]	Deng, X.-Y.; Lin, J.-H.; Zheng, J.; Xiao, J.-C. Chem. Commun. 2015, 51,8805.
[6]	Li, L.; Wang, F.; Ni, C.; Hu, J. Angew. Chem., nt. Ed. 2013, 52,12390.
[7]	For a recent example, see: Gao, X.; He, X.; Zhang, X. Chin. J. Org. Chem. 2019, 39,215. (in Chinese)
	( 高兴, 何旭, 张新刚, 有机化学, 2019, 39,215.)
[8]	Zhao, Y.; Huang, W.; Zheng, J.; Hu, J. Org. Lett. 2011, 13,5342. doi: 10.1021/ol202208b pmid: 21910464
[9]	For a review, see: Tao, X.; Sheng, R.; Bao, K.; Wang, Y.; Jin, Y. Chin. J. Org. Chem. 2019, 39,2726. (in Chinese)
	( 陶雪芬, 盛荣, 鲍堃, 王玉新, 金银秀, 有机化学, 2019, 39,2726.)
[10]	Xu, L.; Vicic, D.A. J. Am. Chem. Soc. 2016, 138,2536. doi: 10.1021/jacs.6b00053 pmid: 26883690
[11]	Chang, D.; Gu, Y.; Shen, Q. Chem. -Eur. J. 2015, 21,6074. pmid: 25752832
[12]	Fujita, T.; Sanada, S.; Chiba, Y.; Sugiyama, K.; Ichikawa, J. Org. Lett. 2014, 16,1398. doi: 10.1021/ol5001582 pmid: 24552502
[13]	Hanamoto, T.; Kurosato, F.; Ishikawa, T.; Yamada, Y. Synlett 2015, 26,1827.
[14]	Zafrani, Y.; Sod-Moriah, G.; Segall, Y. Tetrahedron 2009, 65,5278.
[15]	For selected reviews, see: (a) Zhang, Y.; Wang, J. Chem. Commun. 2009, 36,5350. pmid: 32250543
	(b) Xiao, Q.; Zhang, Y.; Wang, J. Acc. Chem. Res. 2013, 46,236. doi: 10.1021/ar300101k pmid: 32250543
	(c) Qiu, D.; Qiu, M.; Ma, R.; Zhang, Y.; Wang, J. Acta Chim. Sinica 2016, 74,472. (in Chinese) pmid: 32250543
	( 邱頔, 邱孟龙, 马戎, 张艳, 王剑波, 化学学报, 2016, 74,472.) pmid: 32250543
	(d) Liu, L.; Zhang, J. Chin. J. Org. Chem. 2017, 37,1117. (in Chinese) pmid: 32250543
	( 刘路, 张俊良, 有机化学, 2017, 37,1117.) pmid: 32250543
	(e) Gao, Y.; Wang, J. Chin. J. Org. Chem. 2018, 38,1275. (in Chinese) pmid: 32250543
	( 郜云鹏, 王剑波, 有机化学, 2018, 38,1275.) pmid: 32250543
	(f) Yang, Z.; Stivanin, M.L.; Jurberg, I.D.; Koenigs, R.M. Chem. Soc. Rev. 2020, 49,6833. doi: 10.1039/d0cs00224k pmid: 32250543
	(g) Zhao, R.; Shi, L. Angew. Chem., nt. Ed. 2020, 59,12282. pmid: 32250543
	(h) Wu, S.; Song, H.-X.; Zhang, C.-P. Chem.-Asian J. 2020, 15,1660. doi: 10.1002/asia.202000305 pmid: 32250543
[16]	Gilman, H.; Jones, R.G. J. Am. Chem. Soc. 1943, 65,1458.
[17]	For a leading review, see: (a) Mykhailiuk, P. K. Chem Rev. 2020, 120,12718.
	For selected references, see: (b) Morandi, B.; Mariampillai, B.; Carreira, E.M. Angew. Chem., nt. Ed. 2011, 50,1101.
	(c) Wu, G.; Deng, Y.; Wu, C.; Wang, X.; Zhang, Y.; Wang, J. Eur. J. Org. Chem. 2014, 2014,4477.
	(d) Luo, H.; Wu, G.; Zhang, Y.; Wang, J. Angew. Chem., nt. Ed. 2015, 54,14503.
	(e) Chen, Z.; Zheng, Y.; Ma, J.-A. Angew. Chem., nt. Ed. 2017, 56,4569.
	(f) Chen, Z.; Ren, N.; Ma, X.; Nie, J.; Zhang, F.-G.; Ma, J.-A. ACS Catal. 2019, 9,4600.
	(g) Li, J.; Zhang, D.; Chen, J.; Ma, C.; Hu, W. ACS Catal. 2020, 10,4559.
[18]	(a) Atherton, J.H.; Fields, R.; Haszeldine, R.N. J. Chem. Soc. C 1971,366. pmid: 25666338
	(b) Mykhailiuk, P.K. Org. Biomol. Chem. 2015, 13,3438. pmid: 25666338
[19]	Mykhailiuk, P.K. Angew. Chem., nt. Ed. 2015, 54,6558.
[20]	Li, J.; Yu, X.-L.; Cossy, J.; Lv, S.-Y.; Zhang, H.-L.; Su, F.; Mykhailiuk, P.K.; Wu, Y. Eur. J. Org. Chem. 2017, 2017,266.
[21]	Zheng, Y.; Yu, X.; Lv, S.; Mykhailiuk, P.K.; Ma, Q.; Hai, L.; Wu, Y. RSC Adv. 2018, 8,5114.
[22]	Lebed, P.S.; Fenneteau, J.; Wu, Y.; Cossy, J.; Mykhailiuk, P.K. Eur. J. Org. Chem. 2017, 2017,6114.
[23]	Feraldi-Xypolia, A.; Fredj, G.; Tran, G.; Tsuchiya, T.; Vors, J.-P.; Mykhailiuk, P.; GomezPardo, D.; Cossy, J. Asian J. Org. Chem. 2017, 6,927.
[24]	Han, W.-Y.; Zhao, J.; Wang, J.-S.; Xiang, G.-Y.; Zhang, D.-L.; Bai, M.; Cui, B.-D.; Wan, N.-W.; Chen, Y.-Z. Org. Biomol. Chem. 2017, 15,5571. pmid: 28639676
[25]	Han, W.-Y.; Zhao, J.; Wang, J.-S.; Cui, B.-D.; Wan, N.-W.; Chen, Y.-Z. Tetrahedron 2017, 73,5806.
[26]	Han, W.-Y.; Zhao, J.; Cui, B.-D.; Chen, Y.-Z. Chin. J. Synth. Chem. 2018, 26,328. (in Chinese)
	( 韩文勇, 赵佳, 崔宝东, 陈永正, 合成化学, 2018, 26,328.)
[27]	Han, W.-Y.; Wang, J.-S.; Zhao, J.; Long, L.; Cui, B.-D.; Wan, N.-W.; Chen, Y.-Z. J. Org. Chem. 2018, 83,6556. pmid: 29863343
[28]	Wang, J.-S.; Shan, J.; Bai, M.; Cui, B.-D.; Wan, N.-W.; Wang, Y.-S.; Han, W.-Y.; Chen, Y.-Z. Tetrahedron 2018, 74,3904.
[29]	Wang, J.-S.; Huang, K.-S.; Han, W.-Y.; Cui, B.-D.; Wan, N.-W.; Chen, Y.-Z. Org. Lett. 2019, 21,8751. doi: 10.1021/acs.orglett.9b03371 pmid: 31642680
[30]	Zhang, X.-W.; Hu, W.-L.; Chen, S.; Hu, X.-G. Org. Lett. 2018, 20,860.
[31]	Gao, Y.; Peng, S.-Q.; Liu, D.-Y.; Rui, P.-X.; Hu, X.-G. Eur. J. Org. Chem. 2019, 2019,1715.
[32]	Mykhailiuk, P.K.; Kishko, I.; Kubyshkin, V.; Budisa, N.; Cossy, J. Chem.-Eur. J. 2017, 23,13279. pmid: 28753245
[33]	Peng, S.-Q.; Zhang, X.-W.; Zhang, L.; Hu, X.-G. Org. Lett. 2017, 19,5689. pmid: 28981298
[34]	Li, J.; Ma, C.; Xing, D.; Hu, W. Org. Lett. 2019, 21,2101. doi: 10.1021/acs.orglett.9b00382 pmid: 30888191
[35]	Mertens, L.; Hock, K.J.; Koenigs, R.M. Chem.-Eur. J. 2016, 22,9542. pmid: 27168358
[36]	Hock, K.J.; Mertens, L.; Koenigs, R.M. Chem. Commun. 2016, 52,13783.
[37]	Hock, K.J.; Mertens, L.; Metze, F.K.; Schmittmann, C.; Koenigs, R.M. Green Chem. 2017, 19,905.
[38]	Britton, J.; Jamison, T.F. Angew. Chem., nt. Ed. 2017, 56,8823.
[39]	Britton, J.; Jamison, T.F. Eur. J. Org. Chem. 2017, 2017,6566.
[40]	Duan, Y.; Lin, J.-H.; Xiao, J.-C.; Gu, Y.-C. Chem. Commun. 2017, 53,3870.
[41]	Duan, Y.; Lin, J.-H.; Xiao, J.-C.; Gu, Y.-C. Org. Chem. Front. 2017, 4,1917.
[42]	Pan, X.-Y.; Zhao, Y.; Qu, H.-A.; Lin, J.-H.; Hang, X.-C.; Xiao, J.-C. Org. Chem. Front. 2018, 5,1452.
[43]	Zeng, J.-L.; Chen, Z.; Zhang, F.-G.; Ma, J.-A. Org. Lett. 2018, 20,4562. pmid: 30014703
[44]	Peng, X.; Xiao, M.-Y.; Zeng, J.-L.; Zhang, F.-G.; Ma, J.-A. Org. Lett. 2019, 21,4808. doi: 10.1021/acs.orglett.9b01697 pmid: 31184157
[45]	Zhang, Z.-Q.; Zheng, M.-M.; Xue, X.-S.; Marek, I.; Zhang, F.-G.; Ma, J.-A. Angew. Chem., nt. Ed. 2019, 58,18191.
[46]	Tan, X.-F.; Zhang, F.-G.; Ma, J.-A. Beilstein J. Org. Chem. 2020, 16,638.
[47]	Peng, X.; Zhang, F.-G.; Ma, J.-A. Adv. Synth. Catal. 2020, 362,4432.
[48]	Ning, Y.; Zhang, X.; Gai, Y.; Dong, Y.; Sivaguru, P.; Wang, Y.; Reddy, B.R. P.; Zanoni, G.; Bi, X. Angew. Chem.,Int. Ed. 2020, 59,6473.

二氟甲基重氮甲烷作为含氟砌块的应用研究进展

Recent Progress in the Application of Difluoromethyl Diazomethane as Fluorine-Containing Building Block

RichHTML

PDF

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 22

References 48

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Hu Ma, Danfeng Huang, Kehu Wang, Duoduo Tang, Yang Feng, Yuanyuan Reng, Junjiao Wang, Yulai Hu. Synthesis of 3-Trifluoromethylpyrazole Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3257-3267.
[2]	Rongchao Lei, Wenjie Lan, Mengzhu Li, Bin Fu. A Convenient Approach to Benzosultam-Linked Pyrazole Compounds [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2553-2560.
[3]	Yang Sun, Yang Wang, Zichan Zhang, Ye Qian, Guicheng Luo, Beibei Zhou, Lisha Miao, Yudie Chen, Hong Dai, Baolin Xu, Zhengguang Wu. Synthesis and Bioactivities of Novel Pyrazole Oxime Derivatives Containing 1,3,4-Oxadiazole Group [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1584-1590.
[4]	Zichan Zhang, Yang Sun, Sheng Hua, Baolin Xu, Min Zhang, Qin Zhao, Dandan Zheng, Yang Wang, Jianfeng Ju, Yujun Shi, Hong Dai. Synthesis and Insecticidal Activity of Novel Pyrazole Amides Containing an Isoxazole Moiety [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1435-1443.
[5]	Xiang Chen, Wen-Tao Ouyang, Xiao Li, Wei-Min He. Visible-Light Induced Organophotocatalysis for the Synthesis of Difluoroethylated Benzoxazines [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4213-4219.
[6]	Zhi Tu, Jinsheng Yu, Jian Zhou. Synthesis of (Bromodifluoromethyl)trimethylsilane and Its Applications in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3491-3507.
[7]	Haojie Ma, Fengyuan Zhou, Jinlei Liu, Bo Han, Hua Yang, Yuqi Zhang, Jijiang Wang. Construction of Substituted N-Phenylpyrazoles via a Catalyst- Free and Additive-Free Intermolecular Cyclization Process [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1843-1848.
[8]	Changkai Wang, Tengda Sun, Xuebo Zhang, Xinling Yang, Xingxing Lu, Huan Xu, Fasheng Shi, Li Zhang, Yun Ling. Design, Synthesis and Bioactivity of Novel Fluoropyrazole Hydrazides [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1527-1536.
[9]	Wei Wang, Furan Wu, Yidan Ma, Dan Xu, Gong Xu. Study on Synthesis and Antifungal Activity of Novel Benzamides Containing Substituted Pyrazole Unit [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 607-618.
[10]	Siyu Mu, Hongxia Li, Zhilin Wu, Junmei Peng, Jinyang Chen, Weimin He. Electrocatalytic Three-Component Synthesis of 4-Bromopyrazoles from Acetylacetone, Hydrazine and Diethyl Bromomalonate [J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4292-4299.
[11]	Yunshu Liu, Guodong Zhao, Wenju Wu, Yunze Wang, Yanchao Yu, Jun You, Bo Liu. Study on Asymmetric Conjugate Cyanation of 3,5-Dimethyl-N-α,β-unsaturated Acylpyrazole Catalyzed by Magnesium-Bisoxazoline Complex [J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 208-217.
[12]	Haojie Ma, Xiaoqiang Zhou, Bo Han, Ran Li, Xueyan Hou, Xingyue Ji, Yuqi Zhang, Guosheng Huang, Jijiang Wang. A Catalyst-Free One-Pot Protocol for the Construction of Substituted Sulfonyl Pyrazoles [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3710-3716.
[13]	Jiaoli Ma, Penghu Guo, Jing Li, Xincheng Liao, Huicheng Cheng. Synthesis and Antitumor Activity of Amide Derivatives Containing 1,3,4-Thiadiazole and Pyrazole Moieties [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3214-3222.
[14]	Guanglei Li, Haifeng Huang, Jun Yang, Hongzhen Duan. Progress in the Synthesis of Energetic Salts Based on Pyrazole [J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1466-1488.
[15]	Haojie Ma, Zhou Sun, Jinlei Liu, Xia Zhang, Huali Cui, Yuqi Zhang, Jijiang Wang. CBr₄-Mediated Intermolecular Cyclization Reaction: Efficient Synthesis of Substituted N-Acylpyrazoles [J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4353-4360.