Intermolecular Acylation with Acylphosphonates as Alkyl Radical Receptor under Metal-Free Conditions

doi:10.6023/cjoc202207044

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (12): 4332-4339.DOI: 10.6023/cjoc202207044 Previous Articles Next Articles

Special Issue: 自由基化学专辑

ARTICLES

无金属条件下以酰基膦酸酯为烷基自由基受体的分子间酰化反应

方晶^a, 闵庆强^a, 秦海涛^a^,^*(), 刘峰^a^,^b^,^*()

a 苏州大学药学院江苏省神经精神疾病重点实验室和药物化学系苏州 215123
b 中国科学院上海有机化学研究所有机氟化学重点实验室上海200032

收稿日期:2022-07-30 修回日期:2022-08-26 发布日期:2022-09-08
通讯作者: 秦海涛, 刘峰
基金资助:
国家自然科学基金(22171200)

Intermolecular Acylation with Acylphosphonates as Alkyl Radical Receptor under Metal-Free Conditions

Jing Fang^a, Qingqiang Min^a, Haitao Qin^a(), Feng Liu^a^,^b()

a Jiangsu Key Laboratory of Neuropsychiatric Diseases and Department of Medicinal Chemistry, College of Pharmaceutical Sciences, Soochow University, Suzhou 215123
b Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2022-07-30 Revised:2022-08-26 Published:2022-09-08
Contact: Haitao Qin, Feng Liu
Supported by:
National Natural Science Foundation of China(22171200)

1. .pdf(1474KB)

Abstract

As one of the central functional groups in organic chemistry, carbonyl skeleton can be achieved by many ways, but the intermolecular radical reaction using acyl phosphonate as acyl donor is rarely reported. The acylation reaction between acyl phosphonate as a free radical acceptor and three free radical donors, alkyl aldehyde, Hans ester and alkane, was studied under thermochemical and photochemical conditions, respectively. When alkyl aldehydes and alkanes were used as radical precursors, the intermolecular acylation reaction could proceed smoothly under the conditions of microwave heating and the presence of oxidants. When Hantzsch esters were used as the radical precursors, the intermolecular acylation reaction could take place smoothly under UV irradiation at room temperature.

Key words: acylphosphonate, radical acceptor, intermolecular acylation reaction

Cite this article

Jing Fang, Qingqiang Min, Haitao Qin, Feng Liu. Intermolecular Acylation with Acylphosphonates as Alkyl Radical Receptor under Metal-Free Conditions[J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4332-4339.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 3

References 21

[1]	(a) Beller, M. Catalytic Carbonylation Reactions, Springer, Berlin, Heidelberg, 2006.
	(b) Kollár, L. Modern Carbonylation Methods, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2008.
	(c) Beller, M.; Bolm, C. Transition Metals for Organic Synthesis: Building Blocks and Fine Chemicals, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2008.
[2]	Xu, Z. Z. Fine Chem Raw Mater. Intermed. 2012, 2, 11. (in Chinese)
	( 徐兆瑜, 精细化工原料及中间体, 2012, 2, 11.)
[3]	(a) Li, Y. H.; Hu, Y. Y.; Wu, X. F. Chem. Soc. Rev. 2018, 47, 172. doi: 10.1039/C7CS00529F pmid: 33054191
	(b) You, C.; Li, S. L.; Li, X. X.; Lan, J. L.; Yang, Y. H.; Chung, L. W.; Lv, H.; Zhang, X. M. J. Am. Chem. Soc. 2018, 140, 4977. doi: 10.1021/jacs.8b00275 pmid: 33054191
	(c) Zhao, S. L.; Mankad, N. P. Catal. Sci. Technol. 2019, 9, 3603. doi: 10.1039/C9CY00938H pmid: 33054191
	(d) Peltier, J. L.; Tomás-Mendivil, E.; Tolentino, D. R.; Hansmann, M. M.; Jazzar, R.; Bertrand, G. J. Am. Chem. Soc. 2020, 142, 18336. doi: 10.1021/jacs.0c09938 pmid: 33054191
	(e) Bhattacherjee, D.; Rahman, M.; Ghosh, S.; Bagdi, A. K.; Zyryanov, G. V.; Chupakhin, O. N.; Das, P.; Hajra, A. Adv. Synth. Catal. 2021, 363, 1597. doi: 10.1002/adsc.202001509 pmid: 33054191
	(f) Yin, Z. P.; Shi, W. D.; Wu, X. F. J. Org. Chem. 2022, 54, 13941. pmid: 33054191
[4]	(a) Sekine, M.; Satoh, M.; Yamagata, H.; Hata, T. J. Org. Chem. 1980, 45, 4162. doi: 10.1021/jo01309a019 pmid: 17243793
	(b) Sekine, M.; Kume, A.; Nakajima, M.; Hata, T. Chem. Lett. 1981, 1087. pmid: 17243793
	(c) Sekine, M.; Kume, A.; Hata, T. Tetrahedron Lett. 1981, 37, 3617. doi: 10.1016/0040-4039(96)00661-2 pmid: 17243793
	(d) Maeda, H.; Takahashi, K.; Ohmori, H. Tetrahedron 1988, 54, 12233. doi: 10.1016/S0040-4020(98)00767-4 pmid: 17243793
	(e) Takenaka, N.; Abell, J. P.; Yamamoto, H. J. Am. Chem. Soc. 2007, 129, 742. pmid: 17243793
	(f) Martín, V. L.; Río-Rodríguez, R. D.; Díaz-Tendero, S.; Fernández-Salas, J. A.; Alemán, J. Chem. Commun. 2018, 54, 13941. doi: 10.1039/C8CC07561A pmid: 17243793
	(g) Chang, X. F.; Wang, Q. F.; Wang, Y. M.; Song, H. B.; Zhou, Z. H.; Tang, C. C. Eur. J. Org. Chem. 2013, 2013, 2164. doi: 10.1002/ejoc.201201573 pmid: 17243793
[5]	(a) Kim, S.; Jon, S. Y. Chem. Commun. 1996, 1335. pmid: 24127820
	(b) Neshchadin, D.; Rosspeintner, A.; Griesser, M.; Lang, B.; Mosquera-Vazquez, S.; Vauthey, E.; Gorelik, V.; Liska, R.; Hametner, C.; Ganster, B.; Saf, R.; Moszner, N.; Gescheidt, G. J. Am. Chem. Soc. 2013, 135, 17314. doi: 10.1021/ja404433u pmid: 24127820
[6]	(a) Kiyooka, S.; Kaneko, Y.; Matsue, H.; Hamada, M.; Fujiyama, R. J. Org. Chem. 1990, 55, 5562. doi: 10.1021/jo00308a010
	(b) Curran, D. P.; Liu, H. J. Org. Chem. 1991, 56, 3463. doi: 10.1021/jo00011a001
	(c) Curran, D. P.; Palovich, M. Synlett 1992, 631.
	(d) Curran, D. P.; Diederichsen, U.; Palovich, M. J. Am. Chem. Soc. 1997, 119, 4797. doi: 10.1021/ja970219m
	(e) Diederichsen, U.; Curran, D. P. J. Organomet. Chem. 1997, 531, 9. doi: 10.1016/S0022-328X(96)06677-6
	(f) Pandey, G.; Tiwari, S. K.; Singh, B.; Vankab, K.; Jain, S. Chem. Commun. 2017, 53, 12337. doi: 10.1039/C7CC07529D
	(g) Pandey, G.; Tiwari, S. K.; Singh, P.; Mondal, P. K. Org. Lett. 2021, 23, 7730. doi: 10.1021/acs.orglett.1c02672
[7]	For other carbonyl equivalent radical acceptors, see: (a) Iserloh, U.; Curran, D. P. J. Org. Chem. 1998, 63, 4711. doi: 10.1021/jo980369v
	(b) Kim, S.; Lee, I. Y.; Yoon, J.-Y.; Oh, D. H. J. Am. Chem. Soc. 1996, 118, 5138. doi: 10.1021/ja9600993
	(c) Clive, D. L. J.; Beaulieu, P. L.; Set, L. J. Org. Chem. 1984, 49, 1313. doi: 10.1021/jo00181a046
	(d) Bentrude, W. G.; Darnall, K. R. J. Am. Chem. Soc. 1968, 90, 3588. doi: 10.1021/ja01015a066
	(e) Kim, S.; Lim, K. C.; Kim, S.; Ryu, I. Adv. Synth. Catal. 2007, 349, 527. doi: 10.1002/adsc.200600500
	(f) Zhu, Y. C.; Wen, X. J.; Song, S.; Jiao, N. ACS Catal. 2016, 6, 6465. doi: 10.1021/acscatal.6b02074
	(g) Zeng, X. B.; Wang, X.; Zhang, Y. N.; Zhu, L.; Zhao, Y. Org. Biomol. Chem. 2020, 18, 3734. doi: 10.1039/D0OB00055H
	(h) Wang, X. M.; Yu, M.; Song, H. J.; Liu, Y. X.; Wang, Q. M. Org. Lett. 2021, 23, 8353 doi: 10.1021/acs.orglett.1c03087
[8]	(a) Kajiwara, A.; Konishi, Y.; Morishima, Y.; Schnabel, W.; Kuwata, K.; Kamachi, M. Macromolecules 1993, 26, 1656. doi: 10.1021/ma00059a025
	(b) Jockusch, S.; Koptyug, I. V.; McGarry, P. F.; Sluggett, G. W.; Turro, N. J.; Watkins, D. M. J. Am. Chem. Soc, 1997, 119, 11495. doi: 10.1021/ja971630c
	(c) Rees, M. T. L.; Russell, G. T.; Zammit, M. D.; Davis, T. P. Macromolecules 1998, 31, 1763. doi: 10.1021/ma971370j
[9]	(a) Kim, S.; Cho, C. H.; Lim, C. J. J. Am. Chem. Soc. 2003, 125, 9574. doi: 10.1021/ja036499p
	(b) Goh, K. K. K.; Kim, S.; Zard, S. Z. Org. Lett. 2013, 15, 4818. doi: 10.1021/ol402213k
	(c) Zhang, B. X.; He, J. Y.; Li, Y.; Song, T.; Fang, Y. W.; Li, C. Z. J. Am. Chem. Soc. 2021, 143, 4955. doi: 10.1021/jacs.1c02629
[10]	Bonet, Á. G.; Gaspar, A. F.; Martin, R. J. Am. Chem. Soc. 2013, 135, 12576. doi: 10.1021/ja4068707
[11]	Johannes, C. L. W.; Martin, O. Angew. Chem., Int. Ed. 2019, 58, 15386. doi: 10.1002/anie.201909852
[12]	Zhang, X. Y.; Wang, Z. X.; Fan, X. S.; Wang, J. J. J. Org. Chem. 2015, 80, 10660. doi: 10.1021/acs.joc.5b01824
[13]	Wang, L.; Wang, T.; Cheng, G. J.; Li, X. B.; Wei, J. J.; Guo, B.; Zheng, C. J.; Chen, G. Y.; Ran, C. Z.; Zheng, C. ACS Catal. 2020, 10, 7543. doi: 10.1021/acscatal.0c02105
[14]	Wang, C. A.; Rahman, M. M.; Bisz, E.; Dziuk, B.; Szostak, R.; Szostak, M. ACS Catal. 2022, 12, 2426. doi: 10.1021/acscatal.1c05738
[15]	Li, X. J.; Zou, G. J. Organomet Chem. 2015, 794, 136. doi: 10.1016/j.jorganchem.2015.07.009
[16]	Pang, Y. B.; Liu, G. T.; Huang, C. C.; Yuan, X.-A.; Li, W. P.; Xie, J. Angew. Chem., Int. Ed. 2020, 59, 12789. doi: 10.1002/anie.202004950
[17]	Allwood, D. M.; Blakemore, D. C.; Ley, S. V. Org. Lett. 2014, 16, 3064. doi: 10.1021/ol5011714 pmid: 24819872
[18]	Polidano, K.; Allen, B. D. W.; Williams, J. M. J.; Morrill, L. C. ACS Catal. 2018, 8, 6440. doi: 10.1021/acscatal.8b02158
[19]	Dingwall, P.; Greb, A.; Crespin, L. N. S.; Labes, R.; Musio, B.; Poh, J.-S.; Pasau, P.; Blakemorec, D. C.; Ley, S. V. Chem. Commun. 2018, 54, 11685. doi: 10.1039/C8CC06202A
[20]	Sasano, Y.; Murakami, K.; Nishiyama, T.; Kwon, E.; Iwabuchi, Y. Angew. Chem., Int. Ed. 2013, 52, 12624. doi: 10.1002/anie.201307144
[21]	Gao, K. C.; Xu, M.; Cai, C.; Ding, Y. H.; Chen, J. H.; Liu, B. S.; Xia, Y. Z. Org. Lett. 2020, 22, 6055. doi: 10.1021/acs.orglett.0c02117

无金属条件下以酰基膦酸酯为烷基自由基受体的分子间酰化反应

Intermolecular Acylation with Acylphosphonates as Alkyl Radical Receptor under Metal-Free Conditions

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 3

References 21

Related Articles 0

Recommended Articles

Metrics

Comments