4-Substituted Hantzsch Esters as Alkylation Reagents in Organic Synthesis

doi:10.6023/A19050170

Acta Chimica Sinica ›› 2019, Vol. 77 ›› Issue (9): 814-831.DOI: 10.6023/A19050170 Previous Articles Next Articles

Special Issue: 有机自由基化学

Review

4-取代的汉斯酯(Hantzsch Esters)作为烷基化试剂参与的有机反应

叶盛青^a, 吴劼^a^b^c^*()

^a台州学院医药化工与材料工程学院台州 318000
^b复旦大学化学系上海 200438
^c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上海 200032

投稿日期:2019-05-12 发布日期:2019-06-12
通讯作者: 吴劼 E-mail:Jie_wu@fudan.edu.cn
作者简介:叶盛青, 2008年在复旦大学化学系获学士学位; 2013年在复旦大学有机化学专业获理学博士学位(导师: 吴劼教授); 2013年至2015年在美国The Scripps Research Institute从事博士后工作(导师: 余金权教授); 2015年至2019年在苏州诺华制药科技有限公司担任工艺经理; 2019年至今在台州学院医药化工与材料工程学院任副教授. 主要从事类天然产物小分子骨架的有机方法学研究.|吴劼, 1991~1995年就读于江西师范大学化学系, 1995~2000年在中国科学院上海有机化学研究所进行研究生学习(2000年获得博士学位), 2000至2004 年先后在美国哈佛大学(博士后)、洛克菲勒大学艾伦·戴蒙德艾滋病研究中心(访问科学家)及VivoQuest, Inc.(研究员)从事有机合成、药物化学及相关研究工作, 2004年9月回国加入复旦大学化学系(副教授), 2006年4月晋升为教授. 2019年8月加入台州学院医药化工与材料工程学院. 目前主要研究领域: 构建类天然小分子化合物用于抗肿瘤及免疫类疾病、炎症疾病和神经退行性疾病新药研究.
基金资助:
项目受国家自然科学基金资助(Nos.21672037);项目受国家自然科学基金资助(21532001)

4-Substituted Hantzsch Esters as Alkylation Reagents in Organic Synthesis

Ye, Shengqing^a, Wu, Jie^a^b^c^*()

^aSchool of Pharmaceutical and Materials Engineering, Taizhou University, Taizhou 318000, China
^bDepartment of Chemistry, Fudan University, Shanghai 200438, China
^c State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

Received:2019-05-12 Published:2019-06-12
Contact: Wu, Jie E-mail:Jie_wu@fudan.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China(Nos.21672037);Project supported by the National Natural Science Foundation of China(21532001)

Hantzsch Esters were first synthesized by Arthur Rudolf Hantzsch in 1881, and widely used in pharmaceutical chemistry. The application of Hantsch Esters in organic synthesis in the early time was mainly focused on the dehydrogenation of 1,4-dihydrogen pyridines (DHPs) in the synthesis of functional pyridines. In 1955, Mauzerall and Westheimer found that Malachite Green could be reduced by Hantzsch Esters to generate the hydrogenated product. Then these DHPs were extensively used as a reductant for decades due to their electron and hydrogen donating properties. In recent years, scientist found that C—C bond cleavage at 4-position of 4-substituted Hantzsch Esters would lead alkyl transfer, and the alkylation process was a radical process. With the rapid development of free radical chemistry, various alkylation reactions using 4-substituted Hantzsch Esters as alkylation reagent have been developed, such as addition reactions of imines and alkenes; cross-coupling reactions with aryl halides; substitution reactions with functional aromatics; Tsuji-Trost reaction; radical insertion with sulfur dioxide; and asymmetric alkylation etc. The advantages in alkylation transfer by using 4-substituted Hantzsch Esters as alkyl source in the past five years were witnessed dramatically: (1) Highly toxic alkyl metal reagents could be avoided in the alkylation reactions; (2) Compared with the moisture sensitivity of alkyl metal reagents Hantzsch Esters are easily handling; (3) 1,4-Dihydrogen pyridines (DHPs) are biologically-inspired model molecular of reduced nicotinamide adenine dinucleotide (NADH), which would expand the application in biosynthesis. A brief summary in this field is presented in this review, and the advances are classified according to different reaction types. Although these creativity works were developed, there are still some challenges: (1) Could aromatic groups at 4-position of 4-substituted Hantzsch Esters serve as arylation reagents? (2) How to recover the rest pyridine part of Hantzsch Esters after alkylation; (3) New type reactions need to be developed for the asymmetric synthesis.

Key words: 4-substituted Hantzsch Ester, 1,4-dihydropyridine, free radical, alkylation

Cite this article

Ye, Shengqing, Wu, Jie. 4-Substituted Hantzsch Esters as Alkylation Reagents in Organic Synthesis[J]. Acta Chimica Sinica, 2019, 77(9): 814-831.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 31

Scheme 1. Hydrongen and alkyl transfer of DHPs

Scheme 2. Lewis acid catalyzed alkylation of imine

Scheme 3. Radical alkylation of imines catalyzed by photocatalyst

Scheme 4. Radical alkylation of olefins catalyzed by photocatalyst

Scheme 5. Alkylation of olefins catalyzed by organo-photocatalyst

Scheme 6. Alkylation of olefins co-catalyzed by Lewis acid and organo-photocatalyst

Scheme 7. Generation of alkyl radicals from direct excitation of DHPs

Scheme 8. Radical/polar annulation reactions

Scheme 9. Defluorinative alkylation of 1-trifluoromethyl alkenes with alkyl radicals

Scheme 10. Alkylation of alkyl bromide compounds

Scheme 11. Alkylation of aryl halides

Scheme 12. Photoredox/Nickel co-catalyzed alkylation of aryl halides

Scheme 13. Synthesis of arylated saccharides through Nickel and Photoredox dual catalysis

Scheme 14. Synthesis of acylated saccharides through Nickel and Photoredox dual catalysis

Scheme 15. Cross-coupling of alkenyl halides through Nickel and Photoredox dual catalysis

Scheme 16. Cross-coupling of aryl bromide through Nickel catalysis

Scheme 17. Alkynylation with alkyl radicals

Scheme 18. Visible light promoted alkynylation with alkyl radicals

Scheme 19. Replacing the nitro group of nitro-olefins

Scheme 20. Aromatic substitution reactions of cyanoarenes with alkyl radicals

Scheme 21. Desulfonative alkylation of N-heteroaryl sulfones

Scheme 22. Alkylation of (η6-arene)tricarbonylmanganese complexes

Scheme 23. Alkylation of N-heteroaryl complexes

Scheme 24. Single-electron Tsuji-Trost reaction with alkyl radicals

Scheme 25. Insertion of sulfur dioxide with alkyl radicals

Scheme 26. Insertion of sulfur dioxide and electron-deficient alkenes with alkyl readicals

Scheme 27. Stereoselective addition of enals with alkyl radicals

Scheme 28. Stereoselective addition of enals with acyl radicals

Scheme 29. Enantioselective β-alkylation electron-deficient alkenes catalyzed by chiral photoredox catalyst

Scheme 30. Enantioselective allylic alkylation

Scheme 31. Enantioselective alkylation of C=O bond

References 42

[1]	Hantzsch, A . Ber. Dtsch. Chem. Ges. 1881, 14, 1637. doi: 10.1002/(ISSN)1099-0682
[2]	(a) Janis, R. A.; Triggle, D. J. J. Med. Chem. 1983, 25, 775. doi: 10.1021/jm00159a007
	(b) Bocker, R. H.; Guengerich, F. P. J. Med. Chem. 1986, 29, 1596. doi: 10.1021/jm00159a007
	(c) Xie, W.; Wu, Y.; Zhang, J.; Mei, Q.; Zhang, Y.; Zhu, N.; Liu, R.; Zhang, H. Eur. J. Med. Chem. 2018, 145, 35. doi: 10.1021/jm00159a007
	(d) Xie, W.; Zhang, H.; He, J.; Zhang, J.; Yu, Q.; Luo, C.; Li, S. Bioorg. Med. Chem. Lett. 2017, 27, 530. doi: 10.1021/jm00159a007
[3]	Bergstrom, F. W. Chem. Rev. 1944, 35, 77. doi: 10.1021/cr60111a001
[4]	Mauzerall, D.; Westheimer, F. H. J. Am. Chem. Soc. 1955, 77, 2261. doi: 10.1021/ja01613a070
[5]	For selected reviews see: (a) Ouellet, S. G.; Walji, A. M.; Macmillan, D. W. C. Acc. Chem. Res. 2007, 40, 1327. doi: 10.1021/ar7001864
	(b) de Vries, J. G.; Mrsic, N. Catal. Sci. Technol. 2011, 1, 727. doi: 10.1021/ar7001864
	(c) Zheng, C.; You, S.-L. Chem. Soc. Rev. 2012, 41, 2498. doi: 10.1021/ar7001864
	(d) Huang, W.; Cheng, X.. Synlett 2017, 28, 148. doi: 10.1021/ar7001864
	(e) Li, X.; Meng, Y.; Yi, P.; Stepień, M.; Chmielewski, P. J. Angew. Chem., Int. Ed. 2017, 56, 10810. doi: 10.1021/ar7001864
[6]	Loev, B.; Snader, K. M . J. Org. Chem., 1965, 30 1914.
[7]	Wei, Z.; Li, J.; Wang, Z.; Li, P.; Wang, Y . Chin. J. Org. Chem. 2017, 37, 1835 (in Chinese). doi: 10.6023/cjoc201612055
	( 魏振中, 李江飞, 王泽云, 李品华, 王永秋 , 有机化学, 2017, 37, 1835.) doi: 10.6023/cjoc201612055
[8]	For selected examples see:(a) Zou, Y.-Q.; Hörmann, F. M.; Bach, T. Chem. Soc. Rev. 2018, 47, 278. doi: 10.1039/C7CS00509A
	(b) Wang, F.; Chen, P.; Liu, G. Acc. Chem. Res. 2018, 51, 2036. doi: 10.1039/C7CS00509A
	(c) Wang, K.; Kong, W. Chin. J. Chem. 2018, 36, 247. doi: 10.1039/C7CS00509A
	(d) Qiu, S.; Wang, C.; Xie, S.; Huang, X.; Chen, L.; Zhao, Y.; Zeng, Z. Chem. Commun. 2018, 54, 11383. doi: 10.1039/C7CS00509A
	(e) Xie, L.-Y.; Peng, S.; Liu, F.; Chen, G.-R.; Xia, W.; Yu, X.; Li, W.-F.; Cao, Z.; He, W.-M. Org. Chem. Front. 2018, 5, 2604. doi: 10.1039/C7CS00509A
	(f) Lu, L.-H.; Zhou, S.-J.; He, W.-B.; Xia, W.; Chen, P.; Yu, X.; Xu, X.; He, W.-M. Org. Biomol. Chem. 2018, 16, 9064. doi: 10.1039/C7CS00509A
	(g) Zheng, Y.; Liu, M.; Qiu, G.; Xie, W.; Wu, J. Tetrahedron 2019, 75, 1663. doi: 10.1039/C7CS00509A
	(h) Liu, K.-J.; Jiang, S.; Lu, L.-H.; Tang, L.-L.; Tang, S.-S.; Tang, H.-S.; Tang, Z.; He, W.-M.; Xu, X. Green Chem. 2018, 20, 3038. doi: 10.1039/C7CS00509A
	(i) Xie, L.-Y.; Peng, S.; Liu, F.; Yi, J.-Y.; Wang, M.; Tang, Z.; Xu, X.; He, W.-M. Adv. Synth. Catal. 2018, 360, 4259. doi: 10.1039/C7CS00509A
	(j) Xie, L.-Y.; Peng, S.; Liu, F.; Chen, G.-R.; Xia, W.; Yu, X.; Li, W.-F.; Cao, Z.; He, W.-M. Org. Chem. Front. 2018, 5, 2604. doi: 10.1039/C7CS00509A
	(k) Guo, T.; Wei, X.-N.; Liu, Y.; Zhang, P.-K.; Zhao, Y.-H. Org. Chem. Front. 2019, 6, 1414. 1414. doi: 10.1039/C7CS00509A
[9]	For selected examples see: (a) Yoon, T. P.; Ischay, M. A.; Du, J . Nat. Chem. 2010, 2, 527. doi: 10.1038/nchem.687
	(b) Teplý, F. Collect. Czech. Chem. Commun. 2011, 76, 859. doi: 10.1038/nchem.687
	(c) Narayanam, J. M.; Stephenson, C. R. Chem. Soc. Rev. 2011, 40, 102. doi: 10.1038/nchem.687
	(d) Xuan, J.; Xiao, W. J. Angew. Chem., Int. Ed. 2012, 51, 6828. doi: 10.1038/nchem.687
	(e) Shi, L.; Xia, W. Chem. Soc. Rev. 2012, 41, 7687. doi: 10.1038/nchem.687
	(f) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. Chem. Rev. 2013, 113, 5322. doi: 10.1038/nchem.687
	(g) Xi, Y.; Yi, H.; Lei, A. Org. Biomol. Chem. 2013, 11, 2387. doi: 10.1038/nchem.687
	(h) Xuan, J.; Lu, L. Q.; Chen, J. R.; Xiao, W. J. Eur. J. Org. Chem. 2013, 6755. doi: 10.1038/nchem.687
	(i) Hari, D. P.; König, B. Angew. Chem., Int. Ed. 2013, 52, 4734. doi: 10.1038/nchem.687
	(j) Hopkinson, M. N.; Sahoo, B.; Li, J. L.; Glorius, F. Chem. Eur. J. 2014, 20, 3874. doi: 10.1038/nchem.687
	(k) Peñ-López, M.; Rosas-Hernández, A.; Beller, M. Angew. Chem., Int. Ed. 2015, 54, 5006. doi: 10.1038/nchem.687
	(l) Shaw, M. H.; Twilton, J.; MacMillan, D. W. C. J. Org. Chem. 2016, 81, 6898. doi: 10.1038/nchem.687
	(m) Wang, D.; Zhang, L.; Luo, S. Acta Chim. Sinica 2017, 75, 22 (in Chinese) doi: 10.1038/nchem.687
	(王德红, 张龙, 罗三中, 化学学报, 2017, 75, 22.) doi: 10.1038/nchem.687
[10]	Li, G.; Chen, R.; Wu, L.; Fu, Q.; Zhang, X.; Tang, Z. Angew. Chem., Int. Ed. 2013, 52, 8432. doi: 10.1002/anie.v52.32
[11]	Zhang, H.-H.; Yu, S . J. Org. Chem. 2017, 82, 9995. doi: 10.1021/acs.joc.7b01425
[12]	Gu, F.; Huang, W.; Liu, X.; Chen, W.; Cheng, X. Adv. Synth. Catal. 2017, 360, 925. doi: 10.1002/adsc.v360.5
[13]	Wu, Q.-Y.; Min, Q.-Q.; Ao, G.-Z.; Liu, F. Org. Biomol. Chem. 2018, 16, 6391. doi: 10.1039/C8OB01641K
[14]	Mcdonald, B. R.; Scheidt, K. A . Org. Lett. 2018, 20, 6881.
[15]	Van Leeuwen, T.; Buzzetti, L.; Perego, L. A.; Melchiorre, P. Angew. Chem., Int. Ed. 2019, 58, 4953. doi: 10.1002/anie.201814497
[16]	Milligan, J. A.; Phelan, J. P.; Polites, V. C.; Kelly, C. B.; Molander, G. A . Org. Lett. 2018, 20, 6840. doi: 10.1021/acs.orglett.8b02968
[17]	Chen, H.; Anand, D.; Zhou, L . Asian J. Org. Chem. 2019, 8, 661. doi: 10.1002/ajoc.v8.5
[18]	Chen, W.; Liu, Z.; Tian, J.; Li, J.; Ma, J.; Cheng, X.; Li, G. J. Am. Chem. Soc. 2016, 138, 12312. doi: 10.1021/jacs.6b06379
[19]	Nakajima, K.; Nojima, S.; Nishibayashi, Y. Angew. Chem., Int. Ed. 2016, 55, 14106. doi: 10.1002/anie.v55.45
[20]	Gutiérrez-Bonet, Á.; Tellis, J. C.; Matsui, J. K.; Vara, B. A.; Molander, G. A. ACS Catal. 2016, 6, 8004. doi: 10.1021/acscatal.6b02786
[21]	Dumoulin, A.; Matsui, J. K.; Gutiérrez-Bonet, Á.; Molander, G. A. Angew. Chem., Int. Ed. 2018, 57, 6614. doi: 10.1002/anie.201802282
[22]	Badir, S. O.; Dumoulin, A.; Matsui, J. K.; Molander, G. A. Angew. Chem., Int. Ed. 2018, 57, 6610. doi: 10.1002/anie.201800701
[23]	Nakajima, K.; Guo, X.; Nishibayashi, Y . Chem. Asian J. 2018, 13, 3653. doi: 10.1002/asia.v13.23
[24]	Buzzetti, L.; Prieto, A.; Roy, S. R.; Melchiorre, P. Angew. Chem., Int. Ed. 2017, 56, 15039. doi: 10.1002/anie.201709571
[25]	For selected examples see: (a) Wu, C.; Lu, L.-H.; Peng, A.-Z.; Jia, G.-K.; Peng, C.; Cao, Z.; Tang, Z.; He, W.-M.; Xu, X . Green Chem. 2018, 20, 3683. doi: 10.1039/C8GC00491A
	(b) Lu, L.-H.; Zhou, S.-J.; Sun, M.; Chen, J.-L.; Xia, W.; Yu, X.; Xu, X.; He, W.-M. ACS Sustainable Chem. Eng. 2019, 7, 1574. doi: 10.1039/C8GC00491A
	(c) Wu, C.; Xiao, H.-J.; Wang, S.-W.; Tang, M.-S.; Tang, Z.-L.; Xia, W.; Li, W.-F.; Zhong, C.; He, W.-M. ACS Sustainable Chem. Eng.. 2019, 7, 2169. doi: 10.1039/C8GC00491A
	(d) Wu, C.; Wang, Z.; Hu, Z.; Zeng, F.; Zhang, X.-Y.; Cao, Z.; Tang, Z.; He, W.-M.; Xu, X. Org. Biomol. Chem.. 2018, 16, 3177. doi: 10.1039/C8GC00491A
	(e) Wang, Z.; Yang, L.; Liu, H.-L.; Tan, Y.-Z.; Bao, W.-H.; Wang, M.; Tang, Z.; He, W.-M. Chin. J. Org. Chem. 2018, 38, 2639 (in Chinese) doi: 10.1039/C8GC00491A
	(王峥, 杨柳, 刘慧兰, 谭英芝, 包文虎, 汪明, 唐子龙, 何卫民, 有机化学, 2018, 38, 2639.) doi: 10.1039/C8GC00491A
[26]	Liu, X.; Liu, R.; Dai, J.; Cheng, X.; Li, G . Org. Lett. 2018, 20, 6906. doi: 10.1021/acs.orglett.8b03050
[27]	Song, Z.-Y.; Zhang, C.-L.; Ye, S. Org. Biomol. Chem. 2019, 17, 181. doi: 10.1039/C8OB02912A
[28]	Li, G.; Wu, L.; Lv, G.; Liu, H.; Fu, Q.; Zhang, X.; Tang, Z . Chem. Commun. 2014, 50, 6246. doi: 10.1039/C4CC01119H
[29]	Nakajima, K.; Nojima, S.; Sakata, K.; Nishibayashi, Y . ChemCatChem 2016, 8, 1028. doi: 10.1002/cctc.v8.6
[30]	Wang, Z.-J.; Zheng, S.; Matsui, J. K.; Liu, Z.; Molander, G. A. Chem. Sci. 2019, 10, 4389. doi: 10.1039/C9SC00776H
[31]	Cao, L.; Zheng, L.; Huang, Q. J. Organomet. Chem. 2014, 768, 56. doi: 10.1016/j.jorganchem.2014.06.021
[32]	For selected examples see: (a) Xie, L.-Y.; Peng, S.; Tan, J.-X.; Sun, R.-X.; Yu, X.; Dai, N.-N.; Tang, Z.-L.; Xu, X.; He, W.-M. ACS Sustainable Chem. Eng. 2018, 6, 16976. doi: 10.1021/acssuschemeng.8b04339
	(b) Xie, L.-Y.; Peng, S.; Lu, L.-H.; Hu, J.; Bao, W.-H.; Zeng, F.; Tang, Z.; Xu, X.; He, W.-M. ACS Sustainable Chem. Eng. 2018, 6, 7989. doi: 10.1021/acssuschemeng.8b04339
	(c) Xie, L.-Y.; Peng, S.; Jiang, L.-L.; Peng, X.; Xia, W.; Yu, X.; Wang, X.-X.; Cao, Z.; He, W.-M. Org. Chem. Front. 2019, 6, 167. doi: 10.1021/acssuschemeng.8b04339
[33]	Gutiérrez-Bonet, Á.; Remeur, C.; Matsui, J. K.; Molander, G. A. J. Am. Chem. Soc. 2017, 139, 12251. doi: 10.1021/jacs.7b05899
[34]	Matsui, J. K.; Gutiérrez-Bonet, Á.; Rotella, M.; Alam, R.; Gutierrez, O.; Molander, G. A. Angew. Chem., Int. Ed. 2018, 57, 15847. doi: 10.1002/anie.201809919
[35]	For selected examples see: (a) Gong, X.; Wang, M.; Ye, S.; Wu, J . Org. Lett. 2019, 21, 1156. doi: 10.1021/acs.orglett.9b00100
	(b) Ye, S.; Qiu, G.; Wu, J . Chem. Commun. 2019, 55, 1013. doi: 10.1021/acs.orglett.9b00100
	(c) Ye, S.; Zheng, D.; Wu, J.; Qiu, G. Chem. Commun. 2019, 55, 2214. doi: 10.1021/acs.orglett.9b00100
	(d) Ye, S.; Li, Y.; Wu, J.; Li, Z. Chem. Commun. 2019, 55, 2489. doi: 10.1021/acs.orglett.9b00100
	(e) Gong, X.; Li, X.; Xie, W.; Wu, J.; Ye, S. Org. Chem. Front. 2019, 6, 1863. doi: 10.1021/acs.orglett.9b00100
	(f) Zhang, J.; Xie, W.; Ye, S.; Wu, J. Org. Chem. Front. 2019, 6, 2254. doi: 10.1021/acs.orglett.9b00100
	(g) Ye, S.; Xiang, T.; Li, X.; Wu, J. Org. Chem. Front. 2019, 6, 2183. doi: 10.1021/acs.orglett.9b00100
	(h) Ye, S.; Li, X.; Xie, W.; Wu, J. Asian J. Org. Chem. 2019, 8, 893. doi: 10.1021/acs.orglett.9b00100
	(i) Ye, S.; Li, X.; Xie, W.; Wu, J. Eur. J. Org. Chem. 2019, 10.1002/ejoc.201900396. doi: 10.1021/acs.orglett.9b00100
	(j) Zhang, J.; Li, X.; Xie, W.; Ye, S.; Wu, J. Org. Lett. 2019, 21, DOI: 10.1021/acs.orglett.9b01323. doi: 10.1021/acs.orglett.9b00100
	(k) Zong, Y.; Lang, Y.; Yang, M.; Li, X.; Fan, X.; Wu, J. Org. Lett. 2019, 21, 1935. doi: 10.1021/acs.orglett.9b00100
[36]	Wang, X.; Li, H.; Qiu, G.; Wu, J . Chem. Commun. 2019, 55, 2062. doi: 10.1039/C8CC10246E
[37]	Wang, X.; Yang, M.; Xie, W.; Fan, X.; Wu, J . Chem. Commun. 2019, 55, 6010. doi: 10.1039/C9CC03004B
[38]	Verrier, C.; Alandini, N.; Pezzetta, C.; Moliterno, M.; Buzzetti, L.; Hepburn, H. B.; Vega-Penaloza, A.; Silvi, M.; Melchiorre, P . ACS Catal. 2018, 8, 1062. doi: 10.1021/acscatal.7b03788
[39]	Goti, G.; Bieszczad, B.; Vega-Penaloza, A.; Melchiorre, P. Angew. Chem., Int. Ed. 2019, 58, 1213. doi: 10.1002/anie.201810798
[40]	de Assis, F. F.; Huang, X.; Akiyama, M.; Pilli, R. A.; Meggers, E. J. Org. Chem. 2018, 83, 10922. doi: 10.1021/acs.joc.8b01588
[41]	Zhang, H.-H.; Zhao, J.-J.; Yu, S. J. Am. Chem. Soc. 2018, 140, 16914. doi: 10.1021/jacs.8b10766
[42]	Li, F.; Tian, D.; Fan, Y.; Lee, R.; Lu, G.; Yin, Y.; Qiao, B.; Zhao, X.; Xiao, Z.; Jiang, Z . Nat. Commun. 2019, DOI: 10.1038/s41467-019- 09857-9.

4-取代的汉斯酯(Hantzsch Esters)作为烷基化试剂参与的有机反应

4-Substituted Hantzsch Esters as Alkylation Reagents in Organic Synthesis

RichHTML

PDF

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 31

References 42

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Shan Li, Junxin Lu, Jie Liu, Lvqi Jiang, Wenbin Yi. Electrochemical Synthesis of α-Fluoroalkylated Ketones using Sodium Fluoroalkylsulfinate [J]. Acta Chimica Sinica, 2024, 82(2): 110-114.
[2]	Li Liu, Gang Zheng, Guoqiang Fan, Hongguang Du, Jiajing Tan. Research Progress in Organic Reactions Involving 4-Acyl/Carbamoyl/Alkoxycarbonyl Substituted Hantzsch Esters [J]. Acta Chimica Sinica, 2023, 81(6): 657-668.
[3]	Yating Zhao, Fan Liu, Qiuan Wang, Wujiong Xia. Visible-Light-Promoted N-Alkylation Reactions of (aza)Aromatic Amines with Ethyl Diazoacetate [J]. Acta Chimica Sinica, 2023, 81(2): 111-115.
[4]	Jianqiang Chen, Gangguo Zhu, Jie Wu. Recent Advances in Radical-Based Dehydroxylation of Hydroxyl Groups via Oxalates [J]. Acta Chimica Sinica, 2023, 81(11): 1609-1623.
[5]	Hongdan Zhang, Xinyu Lan, Peng Cheng. Advances in Hydroxyl Free Radical Assisted Synthesis of Zeolite [J]. Acta Chimica Sinica, 2023, 81(1): 100-110.
[6]	Xiao, Yingxia, Liu, Zhong-Quan. Radical-Promoted Cross Dehydrogenative Coupling of Ketones and Esters with Electron-Rich Heteroarenes [J]. Acta Chimica Sinica, 2019, 77(9): 874-878.
[7]	Dai, Jianling, Lei, Wenlong, Liu, Qiang. Visible-Light-Driven Difluoroalkylation of Aromatics Catalyzed by Copper [J]. Acta Chimica Sinica, 2019, 77(9): 911-915.
[8]	Hai, Man, Guo, Li-Na, Wang, Le, Duan, Xin-Hua. Visible Light Promoted Ketoalkylation of Quinoxaline-2(1H)-ones via Oxidative Ring-Opening of Cycloalkanols [J]. Acta Chimica Sinica, 2019, 77(9): 895-900.
[9]	Zhao, Yong, Li, Shihong, Zhang, Miaomiao, Liu, Feng. Synthesis of β,γ-Unsaturated Esters and γ-Ketone Esters with Amino Acid Ester-Derived Katritzky Salts [J]. Acta Chimica Sinica, 2019, 77(9): 916-921.
[10]	Zhang, Heng, Mou, Xueqing, Chen, Gong, He, Gang. Copper-catalyzed Intramolecular Aminoperfluoroalkylation Reaction of O-Homoallyl Benzimidates [J]. Acta Chimica Sinica, 2019, 77(9): 884-888.
[11]	Zhang Shuo, Hou Zitong, Song Zihe, Su Xiaofeng, Wang Feng, Yu Yitao, Peng Dan, Cui Shiqi, Liu Yifan, Wang Jiarui, Song Jianjun. Zn/Ni Bimetallic Relay Catalysis: One Pot Intramolecular Cycloisomerization/Intermolecular Amidoalkylation Reaction toward Oxazole Derivatives [J]. Acta Chimica Sinica, 2019, 77(11): 1168-1172.
[12]	Jiao Yang, Zhang Xi. Supramolecular Free Radicals: Fabrication, Modulation and Functions [J]. Acta Chim. Sinica, 2018, 76(9): 659-665.
[13]	Gu Zhengyang, Ji Shunjun. Recent Advances in Cobalt Catalyzed Isocyanide Coupling Reactions [J]. Acta Chim. Sinica, 2018, 76(5): 347-356.
[14]	Zhang Jinlong, Jiang Gaoxi. Synthesis of Non-Natural Amino Acid Derivatives Bearing Triphenylamine Core Skeleton via Pd-Catalyzed Direct Asymmetric Allylic Alkylation [J]. Acta Chim. Sinica, 2018, 76(11): 890-894.
[15]	Zhou Nengneng, Xu Pan, Li Weipeng, Cheng Yixiang, Zhu Chengjian. Visible Light Promoted Carbodifluoroalkylation of Homopropargylic Alcohols via Concomitant 1,4-Aryl Migration [J]. Acta Chim. Sinica, 2017, 75(1): 60-65.