TfOH催化羧酸与α-芳基重氮酯的O—H插入反应

doi:10.6023/cjoc202410026

摘要/Abstract

报道了一种高效的TfOH催化芳基重氮酯与羧酸的O—H插入反应. 该方法不需要过渡金属催化, 且操作简单, 可以在较广的底物范围内以中等到较高的产率一锅法合成各种α-酰氧基酯. 所有的反应原料都很容易获得, 并且该类型的反应可以在室温、空气中进行.

关键词: 羧酸, α-芳基重氮酯, TfOH, O—H插入

An efficient TfOH-catalyzed O—H insertion reaction of α-aryl diazoesters with carboxylic acids is reported. This metal-free protocol provides an operationally simple method for a one-pot assembly of diverse α-acyloxy esters in moderate to high yields with a broad substrate scope. All starting materials are readily available, and the reactions can be conducted in the open air at room temperature.

Key words: carboxylic acids, α-aryl diazoesters, TfOH, O—H insertion

引用此文

陈桂芳, 李红强, 曾幸荣. TfOH催化羧酸与α-芳基重氮酯的O—H插入反应[J]. 有机化学, 2025, 45(7): 2537-2544.

Guifang Chen, Hongqiang Li, Xingrong Zeng. TfOH-Catalyzed O—H Insertion of Carboxylic Acids with α-Aryl Diazoesters[J]. Chinese Journal of Organic Chemistry, 2025, 45(7): 2537-2544.

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参考文献 15

[1]	(a) Zhu J.; Hu W.; Sun S.; Yu J.-T.; Cheng J. Adv. Synth. Catal. 2017, 359, 3725. pmid: 27145029
	(b) Zhang Z.; Yu Y.; Xie Y.; Hughes T.; Xu J.; Huang F.; Huang H. Green Chem. 2020, 22, 4165. pmid: 27145029
	(c) Wang B.; Howard I. G.; Pope J. W.; Conte E. D.; Deng Y. Chem. Sci. 2019, 10, 7958. doi: 10.1039/c9sc02189b pmid: 27145029
	(d) Xue Z.; Li Y.; Luo S. ACS Catal. 2020, 10, 10989. pmid: 27145029
	(e) Steck V.; Carminati D. M.; Johnson N. R.; Fasan R. ACS Catal. 2020, 10, 10967. pmid: 27145029
	(f) Reddy A. C. S.; Choutipalli V. S. K.; Ghorai J.; Subramanian V.; Anbarasan P. ACS Catal. 2017, 7, 6283. pmid: 27145029
	(g) Mancinelli J. P.; Wilkerson-Hill S. M. ACS Catal. 2020, 10, 11171. pmid: 27145029
	(h) Liu Y.; Zhou C.; Xiong M.; Jiang J.; Wang J. Org. Lett. 2018, 20, 5889. pmid: 27145029
	(i) Liu K.; Xu G.; Sun J. Chem. Sci. 2018, 9, 634. pmid: 27145029
	(j) Gutiérrez-Bonet Á.; Juliá-Hernández F.; de Luis B.; Martin R. J. Am. Chem. Soc. 2016, 138, 6384. doi: 10.1021/jacs.6b02867 pmid: 27145029
	(k) Kumar N.; Gola A. K.; Pandey S. K. Org. Biomol. Chem. 2024, 22, 1624. pmid: 27145029
	(l) Qin P.; Ma H.; Zhang F.-G.; Ma J.-A. Acta Chim. Sinica 2023, 81, 697 (in Chinese). pmid: 27145029
	( 秦沛, 马海, 张发光, 马军安, 化学学报, 2023, 81, 697.) doi: 10.6023/A23040154 pmid: 27145029
	(m) Zhao Y.-T.; Liu F.-W.; Q.-A.; Xia W.-J. Acta Chim. Sinica 2023, 81, 111 (in Chinese). pmid: 27145029
	( 赵亚婷, 刘帆, 汪秋安, 夏吾炯, 化学学报, 2023, 81, 111.) doi: 10.6023/A22120490 pmid: 27145029
	(n) Yu L.-F.; Yao X.-Q.; Wang J.-B. Acta Chim. Sinica 2023, 81, 1015 (in Chinese). pmid: 27145029
	( 于乐飞, 姚兴奇, 王剑波, 化学学报, 2023, 81, 1015.) doi: 10.6023/A23050244 pmid: 27145029
[2]	(a) Zhang Y.; Yao Y.; He L.; Liu Y.; Shi L. Adv. Synth. Catal. 2017, 359, 2754.
	(b) Koothradan F. F.; Suresh Babu A.; Pushpakaran K. P.; Jayara- ni A.; Sivasankar C. J. Org. Chem. 2022, 87, 10564.
[3]	(a) Xu Y.; Lv G.; Yan K.; He H.; Li J.; Luo Y.; Lai R.; Hai L.; Wu Y. Chem. Asian J. 2020, 15, 1945. pmid: 22246347
	(b) Wang D.; Xu C.; Zhang L.; Luo S. Org. Lett. 2015, 17, 576. pmid: 22246347
	(c) Ba D.; Wen S.; Tian Q.; Chen Y.; Lv W.; Cheng G. Nat. Commun. 2020, 11, 4219. pmid: 22246347
	(d) Zhang C.; Li H.; Pei C.; Qiu L.; Hu W.; Bao X.; Xu X. ACS Catal. 2019, 9, 2440. pmid: 22246347
	(e) Sreenivasulu M.; Kumar K. S.; Kumar P. R.; Chandrasekhar K. B.; Pal M. Org. Biomol. Chem. 2012, 10, 1670. doi: 10.1039/c2ob06950d pmid: 22246347
	(f) Sharma A. K.; Kumar P.; Vishwakarma R. K.; Singh K. N. Asian J. Org. Chem. 2018, 7, 688. pmid: 22246347
	(g) Miller E. J.; Zhao W.; Herr J. D.; Radosevich A. T. Angew. Chem., Int. Ed. 2012, 51, 10605. pmid: 22246347
[4]	(a) Harada S.; Tanikawa K.; Homma H.; Sakai C.; Ito T.; Nemoto T. Chem.-Eur. J. 2019, 25, 12058.
	(b) Hari D. P.; Waser J. J. Am. Chem. Soc. 2016, 138, 2190.
	(c) Liang X.-S.; Li R.-D.; Wang X.-C. Angew. Chem., Int. Ed. 2019, 58, 13885.
	(d) Massaro N. P.; Stevens J. C.; Chatterji A.; Sharma I. Org. Lett. 2018, 20, 7585.
	(e) Pisella G.; Gagnebin A.; Waser J. Org. Lett. 2020, 22, 3884.
	(f) Shen H.-Q.; Xie H.-P.; Sun L.; Zhou Y.-G. Organometallics 2019, 38, 3902.
	(g) Shi T.; Teng S.; Wei Y.; Guo X.; Hu W. Green Chem. 2019, 21, 4936.
	(h) Suneja A.; Loui H. J.; Schneider C. Angew. Chem., Int. Ed. 2020, 59, 5536.
	(i) Tseberlidis G.; Caselli A.; Vicente R. J. Organomet. Chem. 2017, 835, 1.
	(j) Zeng L.; Sajiki H.; Cui S. Org. Lett. 2019, 21, 6423.
	(k) Zhu S.-F.; Cai Y.; Mao H.-X.; Xie J.-H.; Zhou Q.-L. Nat. Chem. 2010, 2, 546.
[5]	Tan F.; Liu X.; Hao X.; Tang Y.; Lin L.; Feng X. ACS Catal. 2016, 6, 6930.
[6]	Chen Z.-S.; Duan X.-H.; Zhou P.-X.; Ali S.; Luo J.-Y.; Liang Y.-M. Angew. Chem., Int. Ed. 2012, 51, 1370.
[7]	(a) Couch E. D.; Auvil T. J.; Mattson A. E. Chem.-Eur. J. 2014, 20, 8283. pmid: 25564133
	(b) Sreenivasulu M.; Arun Kumar K.; Sateesh Reddy K.; Siva Kumar K.; Rajender Kumar P.; Chandrasekhar K. B.; Pal M. Tetrahedron Lett. 2011, 52, 727. pmid: 25564133
	(c) Yi X.; Feng J.; Huang F.; Baell J. B. Chem. Commun. 2020, 56, 1243. pmid: 25564133
	(d) Zhao W.; Yan P. K.; Radosevich A. T. J. Am. Chem. Soc. 2015, 137, 616. doi: 10.1021/ja511889y pmid: 25564133
[8]	Jana S.; Yang Z.; Li F.; Empel C.; Ho J.; Koenigs R. M. Angew. Chem., Int. Ed. 2020, 59, 5562.
[9]	Jurberg I. D.; Davies H. M. L. Chem. Sci. 2018, 9, 5112. doi: 10.1039/c8sc01165f pmid: 29938043
[10]	(a) Xu G.; Tang S.; Shao Y.; Sun J. Chem. Commun. 2019, 55, 9096.
	(b) Yu Z.; Li Y.; Shi J.; Ma B.; Liu L.; Zhang J. Angew. Chem., Int. Ed. 2016, 55, 14807.
[11]	San H. H.; Wang S.-J.; Jiang M.; Tang X.-Y. Org. Lett. 2018, 20, 4672.
[12]	Empel C.; Nguyen T. V.; Koenigs R. M. Org. Lett. 2021, 23, 548.
[13]	(a) Hu S.; Lu Z.; Liu M.; Xu H.; Wu J.; Chen F. J. Org. Chem. 2020, 85, 14916.
	(b) Zhai C.; Xing D.; Jing C.; Zhou J.; Wang C.; Wang D.; Hu W. Org. Lett. 2014, 16, 2934.
	(c) Gallo R. D. C.; Momo P. B.; Day D. P.; Burtoloso A. C. B. Org. Lett. 2020, 22, 2339.
	(d) Gallo R. D. C.; Burtoloso A. C. B. Green Chem. 2018, 20, 4547.
	(e) Zhang Z.; Yu Y.; Huang F.; Yi X.; Xu Y.; He Y.; Baell J. B.; Huang H. Green Chem. 2020, 22, 1594.
	(f) Chen W.; Chen G.; Wang B.; Wang W.; Huang W.; Tian X. Tetrahedron Lett. 2021, 66, 152751.
[14]	(a) Farshadfar K.; Hashemi A.; Khakpour R.; Laasonen K. ACS Omega 2023, 9, 1106.
	(b) Tan F.; Wang W.; Huang X.; Zhong Y.; Song T.; Wang J.; Mei L. J. Org. Chem. 2024, 89, 2588.
	(c) Kumar N.; Venkatesh R.; Kandasamy J. Org. Biomol. Chem. 2022, 20, 6766.
[15]	Keipour H.; Jalba A.; Delage-Laurin L.; Ollevier T. J. Org. Chem. 2017, 82, 3000. doi: 10.1021/acs.joc.6b02998 pmid: 28132507

Entry	Catalyst	Solvent	Yield^b/%
1	Tf₂NH	CH₂Cl₂	—
2	TfOH	CH₂Cl₂	60
3	TsOH•H₂O	CH₂Cl₂	—
4	TFA	CH₂Cl₂	—
5	TfOH	DCE	64
6	TfOH	CHCl₃	50
7	TfOH	THF	—
8	TfOH	MeCN	13
9	TfOH	Dioxane	32
10^c	TfOH	DCE	29
11^c,d	TfOH	DCE	45
12^c,d	TfOH	DCE	59^e/69^g/80^h/76ⁱ
13^c,d	TfOH	DCE	50^e,f
14^c,d	TfOH	DCE	45^j/63^k

Entry	Catalyst	Solvent	Yield^b/%
1	Tf₂NH	CH₂Cl₂	—
2	TfOH	CH₂Cl₂	60
3	TsOH•H₂O	CH₂Cl₂	—
4	TFA	CH₂Cl₂	—
5	TfOH	DCE	64
6	TfOH	CHCl₃	50
7	TfOH	THF	—
8	TfOH	MeCN	13
9	TfOH	Dioxane	32
10^c	TfOH	DCE	29
11^c,d	TfOH	DCE	45
12^c,d	TfOH	DCE	59^e/69^g/80^h/76ⁱ
13^c,d	TfOH	DCE	50^e,f
14^c,d	TfOH	DCE	45^j/63^k