三乙胺促进的α-卤代酮C-C键断裂:合成α-乙酰氧基芳基酮

doi:10.6023/cjoc201904051

有机化学 ›› 2019, Vol. 39 ›› Issue (11): 3223-3229.DOI: 10.6023/cjoc201904051 上一篇下一篇

研究论文

三乙胺促进的α-卤代酮C-C键断裂:合成α-乙酰氧基芳基酮

王毛锐, 吴雨峥, 姚健, 邓黎, 潘英明, 黄克斌*(), 唐海涛*()

广西师范大学化学与药学院药物资源化学与分子工程国家重点实验室广西桂林 541004

收稿日期:2019-04-22 发布日期:2019-07-03
通讯作者: 黄克斌,唐海涛 E-mail:kbhuang@mailbox.gxnu.edu.cn;httang@gxnu.edu.cn
基金资助:
国家自然科学基金(21362002);中国广西省八桂学者(2016A13)

Triethylamine Promoted the C-C Bond Cleavage of α-Halo Ketones: α-Acetoxyaryl Ketone Synthesis

Wang Maorui, Wu Yuzheng, Yao Jian, Deng Li, Pan Yingming, Huang Kebin*(), Tang Haitao*()

State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin, Guangxi 541004

Received:2019-04-22 Published:2019-07-03
Contact: Huang Kebin,Tang Haitao E-mail:kbhuang@mailbox.gxnu.edu.cn;httang@gxnu.edu.cn
Supported by:
the National Natural Science Foundation of China(21362002);the Bagui Scholar Program of Guangxi Province of China(2016A13)

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摘要/Abstract

C-C键断裂在有机合成中有着重要的作用.报道了一种胺促进的α-卤代酮化合物C-C键断裂的新方法，该方法无需使用过渡金属催化剂以及氧化剂.采用这种方法以廉价的α-卤代酮化合物制备了多种α-乙酰氧基芳基酮化合物.

关键词: C-C键的断裂, α-卤代酮, 无氧化剂和无金属合成, α-乙酰氧基芳基酮

The cleavage of C-C bonds is a key method for synthesis of useful intermediates. A novel amine-promoted C-C bond cleavage of α-halo ketones was reported. Oxidant-free and metal-free conditions are the striking features of the protocol. In this simple method, a variety of α-acetoxyaryl ketone compounds were prepared from commercially available α-halo ketones in good to excellent yields.

Key words: cleavage of C-C bonds, α-halo ketones, oxidant-free and metal-free, α-acetoxyaryl ketone

引用此文

王毛锐, 吴雨峥, 姚健, 邓黎, 潘英明, 黄克斌, 唐海涛. 三乙胺促进的α-卤代酮C-C键断裂:合成α-乙酰氧基芳基酮[J]. 有机化学, 2019, 39(11): 3223-3229.

Wang Maorui, Wu Yuzheng, Yao Jian, Deng Li, Pan Yingming, Huang Kebin, Tang Haitao. Triethylamine Promoted the C-C Bond Cleavage of α-Halo Ketones: α-Acetoxyaryl Ketone Synthesis[J]. Chinese Journal of Organic Chemistry, 2019, 39(11): 3223-3229.

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参考文献 12

[1]	(a) Souillart, L.; Cramer, N. Chem. Rev. 2015, 115, 9410. doi: 10.1021/acs.chemrev.5b00138
	(b) Chen, F.; Wang, T.; Jiao, N. Chem. Rev. 2014, 114, 8613. doi: 10.1021/acs.chemrev.5b00138
	(c) Wang, T.; Jiao, N. Acc. Chem. Res. 2014, 47, 1137. doi: 10.1021/acs.chemrev.5b00138
	(d) Murakami, M.; Ishida, N. J. Am. Chem. Soc. 2016, 138, 13759. doi: 10.1021/acs.chemrev.5b00138
	(e) Tiwari, B.; Zhang, J.; Chi, Y. R. Angew. Chem. Int. Ed. 2012, 51, 1911. doi: 10.1021/acs.chemrev.5b00138
	(f) Sai, M.; Yorimitsu, H.; Oshima, K. Angew. Chem. Int. Ed. 2011, 50, 3294. doi: 10.1021/acs.chemrev.5b00138
	(g) Chen, W.-L.; Wu, S.-Y.; Mo, X.˗L.; Wei, L.˗X.; Liang, C.; Mo, D.˗L. Org. Lett. 2018, 20, 3527. doi: 10.1021/acs.chemrev.5b00138
[2]	(a) Tobisu, M.; Chatani, N. Chem. Soc. Rev. 2008, 37, 300. doi: 10.1039/B702940N
	(b) Qin, C.; Shen, T.; Tang, C.; Jiao, N. Angew. Chem. Int. Ed. 2012, 51, 6971. doi: 10.1039/B702940N
	(c) Qin, C.; Zhou, W.; Chen, F.; Ou, Y.; Jiao, N. Angew. Chem. Int. Ed. 2011, 50, 12595. doi: 10.1039/B702940N
	(d) Klein, J. E. M. N.; Plietker, B. Org. Biomol. Chem. 2013, 11, 1271. doi: 10.1039/B702940N
	(e) Kulinkovich, O. G. Chem. Rev. 2003, 103, 2597. doi: 10.1039/B702940N
	(f) Bart, S. C.; Chirik, P. J. J. Am. Chem. Soc. 2003, 125, 886. doi: 10.1039/B702940N
	(g) Seiser, T.; Cramer, N. J. Am. Chem. Soc. 2010, 132, 5340. doi: 10.1039/B702940N
	(h) Seiser, T.; Saget, T.; Tran, D. N.; Cramer, N. Angew. Chem. Int. Ed. 2011, 50, 7740. doi: 10.1039/B702940N
	(i) Jun, C-H. Chem. Soc. Rev., 2004, 33, 610. doi: 10.1039/B702940N
[3]	(a) Kumar, K. A. A.; Venkateswarlu, V.; Vishwakarma, R. A.; Sawant, S. D. Synthesis 2015, 47, 3161. doi: 10.1055/s-00000084
	(b) Zhang, J.; Jiang, J.; Li, Y.; Zhao, Y.; Wan, X. Org. Lett. 2013, 15, 3222. doi: 10.1055/s-00000084
[4]	Liu L.; Ishida N.; Murakami M. Angew. Chem. Int. Ed. 2012, 51 2485. doi: 10.1002/anie.201108446
[5]	(a) Wang, M.; Lu, J.; Zhang, X.; Li, L.; Li, H.; Luo, N.; Wang, F. ACS Catal. 2016, 6, 6086. doi: 10.1021/acscatal.6b02049
	(b) Liu, H.; Wang, M. Li, H.; Luo, N.; Xu, S.; Wang, F. J. Catal. 2017, 346, 170. doi: 10.1021/acscatal.6b02049
	(c) Wang, M.; Lu, J.; Li, L.; Li, H.; Liu, H.; Wang, F. J. Catal. 2017, 348, 160. doi: 10.1021/acscatal.6b02049
	(d) Anjum, A.; Srinivas, P. Chem. Lett. 2001, 9, 900. doi: 10.1021/acscatal.6b02049
	(e) Baruah, S.; Borthakur, S.; Gogoi, S. Chem. Commun. 2017, 53, 9133. doi: 10.1021/acscatal.6b02049
	(f) Nakamura, R.; Obora, Y.; Ishii, Y. Adv. Synth. Catal. 2009, 351, 1677. doi: 10.1021/acscatal.6b02049
	(g) Minisci, F.; Recupero, F.; Pedulli, G. F.; Lucarini, M. J. Mol. Catal. A 2003, 204~205, 63. doi: 10.1021/acscatal.6b02049
	(h) Minisci, F.; Recupero, F.; Fontana, F.; Bjϕrsvik, H˗R.; Liguori, L. Synlett. 2002, 610. doi: 10.1021/acscatal.6b02049
	(i) Sathyanarayana, P.; Ravi, O.; Muktapuram, P. R.; Bathula, S. R. Org. Biomol. Chem. 2015. 13, 9681. doi: 10.1021/acscatal.6b02049
[6]	(a) Xu, L.; Wang, S.; Chen, B.; Li, M.; Hu, X.; Hu, B.; Jin, L.; Sun, N.; Shen, Z. Synlett. 2018, 1505. doi: 10.1080/00397910500503611
	(b) Shaikh, T. M. A.; Sudalai, A. Eur. J. Org. Chem. 2008, 4877. doi: 10.1080/00397910500503611
	(c) Santaniello, E.; Manzocchi, A.; Farachi, C. Synthesis 1980, 563. doi: 10.1080/00397910500503611
	(d) Lee, J. C.; Lee, J. M. Synth. Commun. 2006, 36, 1071. doi: 10.1080/00397910500503611
	(e) Lee, J. C.; Choi, J. H.; Lee, Y. C. Synlett. 2001, 1563. doi: 10.1080/00397910500503611
[7]	(a) Liu, H.; Li, H.; Lu, J.; Zeng, S.; Wang, M.; Luo, N.; Xu, S.; Wang, F. ACS Catal. 2018, 8, 4761. doi: 10.1021/acscatal.8b00022
	(b) Hirashima, S˗i.; Nobuta, T.; Tada, N.; Itoh, A. Synlett 2009, 2017. doi: 10.1021/acscatal.8b00022
	(c) Yamaguchi, T.; Matsusaki, Y.; Tada, N.; Miura, T.; Itoh, A. Photochem. Photobiol. Sci. 2013, 12, 417. doi: 10.1021/acscatal.8b00022
[8]	(a) Sathyanarayana, P.; Upare, A.; Ravi, O.; Muktapuram, P. R.; Bathula, S. R. RSC Adv. 2016, 6, 22749. doi: 10.1039/C6RA02962K
	(b) Angeles, N. A.; Villavicencio, F.; Guadarrama, C.; Corona, D.; Cuevas˗Yañez, E. J. Braz. Chem. Soc. 2010, 21, 905. doi: 10.1039/C6RA02962K
	(c) Cao, L.; Ding, J.; Gao, M.; Wang, Z.; Li, J.; Wu, A. Org. Lett. 2009, 11, 3810. doi: 10.1039/C6RA02962K
	(d) Rajendar, K.; Kant, R.; Narender, T. Adv. Synth. Catal. 2013, 355, 3591. doi: 10.1039/C6RA02962K
[9]	(a) Caputo, D. F. J.; Arroniz, C.; Dürr, A. B.; Mousseau, J. J.; Stepan, A. F.; Mansfield, S. J.; Anderson, E. A. Chem. Sci. 2018, 9, 5295. doi: 10.1039/C8SC01355A
	(b) Ram, R. N.; Soni, V. K. J. Org. Chem. 2015, 80, 8922. doi: 10.1039/C8SC01355A
	(c) Luo, J.; Zhang, X.; Zhang, J. ACS Catal. 2015, 5, 2250. doi: 10.1039/C8SC01355A
	(d) Xu, G˗C.; Yu, H˗L.; Zhang, X˗Y.; Xu, J˗H. ACS Catal. 2012, 2, 2566. doi: 10.1039/C8SC01355A
	(e) Neumann, M.; Füldner, S.; König, B.; Zeitler, K. Angew. Chem. Int. Ed. 2011, 50, 951. doi: 10.1039/C8SC01355A
	(f) Jiang, H.; Bak, J. R.; López˗Delgado, F. J.; Jørgensen, K. A. Green Chem. 2013, 15, 3355. doi: 10.1039/C8SC01355A
	(g) Zhou, F.; Hu, X.; Gao, M.; Cheng, T.; Liu, G. Green Chem. 2016, 18, 5651. doi: 10.1039/C8SC01355A
	(h) Toma, T.; Shimokawa, J.; Fukuyama, T. Org. Lett. 2007, 9, 3195. doi: 10.1039/C8SC01355A
[10]	Yu S.; Liu S.; Lan Y.; Wan B.; Li X. J. Am. Chem. Soc. 2015, 137 1623. doi: 10.1021/ja511796h
[11]	(a) Tong, W.; Li, W.˗H.; He, Y.; Mo, Z.˗Y.; Tang, H.˗T.; Wang, H.˗S.; Pan, Y.˗M. Org. Lett. 2018, 20, 2494. doi: 10.1021/acs.orglett.8b00886
	(b) He, Y.; Wang, Y.; Liang, X.; Huang, B.; Wang, H.; Pan, Y.˗M.; Org. Lett. 2018, 20, 7117. doi: 10.1021/acs.orglett.8b00886
	(c) Huang, X.˗Y.; Ding, R.; Mo, Z.˗Y.; Xu, Y.˗L.; Tang, H.˗T.; Wang, H.˗S.; Chen, Y.˗Y.; Pan, Y.˗M. Org. Lett. 2018, 20, 4819. doi: 10.1021/acs.orglett.8b00886
	(d) Zhang, B.; Studer, A. Chem. Soc. Rev. 2015, 44, 3505. doi: 10.1021/acs.orglett.8b00886
	(e) Wang, X.; Xiong, W.; Huang, Y.; Zhu, J.; Hu, Q.; Wu, W.; Jiang, H. Org. Lett. 2017, 19, 5818. doi: 10.1021/acs.orglett.8b00886
	(f) Hu, W.; Li, J.; Xu, Y.; Li, J.; Wu, W.; Liu, H.; Jiang, H. Org. Lett. 2017, 19, 678. doi: 10.1021/acs.orglett.8b00886
	(g) Peng, J.; Gao, Y.; Hu, W.; Gao, Y.; Hu, M.; Wu, W.; Ren, Y.; Jiang, H. Org. Lett. 2016, 18, 5924. doi: 10.1021/acs.orglett.8b00886
[12]	(a) Tan, L.; Chen, C.; Liu, W. Beilstein J. Org. Chem. 2017, 13, 1079. doi: 10.3762/bjoc.13.107
	(b) Jia, W˗G.; Zhang, H.; Li, D˗D.; Yan, L˗Q. RSC Adv. 2016, 6, 27590. doi: 10.3762/bjoc.13.107


Entry	Catalyst	Base (equiv.)	Solvent	Yield^b/%
1	Pd(OAc)₂	Et₃N (0.5)	MeCN	44^c
2	—	Et₃N (0.5)	MeCN	46
3	—	Et₃N (1)	MeCN	55
4	—	Et₃N (2)	MeCN	66
5	—	Et₃N (3)	MeCN	60
6	—	Et₂NH (2)	MeCN	45
7	—	(CH₃)₃CNH₂ (2)	MeCN	Trace
8	—	DBU (2)	MeCN	NR
9	—	NaOH (2)	MeCN	NR
10	—	Cs₂CO₃ (2)	MeCN	Trace
11	—	Et₃N (2)	MeCN/H₂O^d	43
12	—	Et₃N (2)	1, 4-Dioxane	NR
13	—	Et₃N (2)	DMF	Trace
14	—	—	N(Et)₃	23
15	—	Et₃N (2)	MeCN	89^e


Entry	Catalyst	Base (equiv.)	Solvent	Yield^b/%
1	Pd(OAc)₂	Et₃N (0.5)	MeCN	44^c
2	—	Et₃N (0.5)	MeCN	46
3	—	Et₃N (1)	MeCN	55
4	—	Et₃N (2)	MeCN	66
5	—	Et₃N (3)	MeCN	60
6	—	Et₂NH (2)	MeCN	45
7	—	(CH₃)₃CNH₂ (2)	MeCN	Trace
8	—	DBU (2)	MeCN	NR
9	—	NaOH (2)	MeCN	NR
10	—	Cs₂CO₃ (2)	MeCN	Trace
11	—	Et₃N (2)	MeCN/H₂O^d	43
12	—	Et₃N (2)	1, 4-Dioxane	NR
13	—	Et₃N (2)	DMF	Trace
14	—	—	N(Et)₃	23
15	—	Et₃N (2)	MeCN	89^e

三乙胺促进的α-卤代酮C-C键断裂:合成α-乙酰氧基芳基酮

Triethylamine Promoted the C-C Bond Cleavage of α-Halo Ketones: α-Acetoxyaryl Ketone Synthesis

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