无配体条件钯催化内炔的氢膦酰化反应合成(E)-烯烃膦酸酯类化合物

doi:10.6023/cjoc202103038

有机化学 ›› 2021, Vol. 41 ›› Issue (8): 3264-3271.DOI: 10.6023/cjoc202103038 上一篇下一篇

研究论文

无配体条件钯催化内炔的氢膦酰化反应合成(E)-烯烃膦酸酯类化合物

许振丽^a, 张宗雪^b, 孟晨湘^b, 张萧雅^b, 许凯^b^,^*(), 刘澜涛^b^,^c, 王涛^b, 徐海云^b, 毛国梁^a^,^*()

a 东北石油大学化学化工学院黑龙江大庆 163318
b 商丘师范学院化学化工学院药物绿色合成河南省工程实验室河南商丘 476000
c 郑州大学化学与分子工程学院郑州 450001

收稿日期:2021-03-22 修回日期:2021-04-13 发布日期:2021-05-08
通讯作者: 许凯, 毛国梁
基金资助:
国家自然科学基金(21572126); 国家自然科学基金(21202095); 河南省技术人员队伍建设(C20150030); 河南省科技创新人才计划(184100510011); 河南省自然科学基金(212300410379); 河南省科技重大专项(192102110222)

Ligand-Free Pd-Catalyzed Hydrophosphorylation of Internal Alkynes for the Synthesis of E-Vinylphosphonates

Zhenli Xu^a, Zongxue Zhang^b, Chenxiang Meng^b, Xiaoya Zhang^b, Kai Xu^b(), Lantao Liu^b^,^c, Tao Wang^b, Haiyun Xu^b, Guoliang Mao^a()

a College of Chemistry and Chemical Engineering, Northeast Petroleum University, Daqing, Heilongjiang 163318
b Henan Engineering Laboratory of Green Synthesis for Pharmaceuticals, College of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu, Henan 476000
c College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001

Received:2021-03-22 Revised:2021-04-13 Published:2021-05-08
Contact: Kai Xu, Guoliang Mao
Supported by:
National Natural Science Foundation of China(21572126); National Natural Science Foundation of China(21202095); Technicians Troop Construction Projects of Henan Province(C20150030); Program of Science and Technology Innovation Talents of Henan Province(184100510011); Natural Science Foundation of Henan Province(212300410379); Key Scientific and Technological Project of Henan Province(192102110222)

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摘要/Abstract

报道了在不同醇中无配体条件下钯催化二苯基H-亚膦酸酯对内炔的氢膦酰化反应合成E-烯烃膦酸酯类化合物的方法. 这种实用且通用的三组分反应涉及二苯基H-亚膦酸酯对相对惰性内炔的顺式加成, 以及伴随的二苯基H-亚膦酸酯的酯交换过程. 反应具有高立体选择性、宽泛的底物范围和无需额外配体等显著特点.

关键词: 加成反应, 三组分反应, 乙烯基膦酸酯, 钯, 内炔

A ligand-free Pd-catalyzed hydrophosphorylation of internal alkynes with diphenyl H-phosphonate in various alcohols for the synthesis of E-vinylphosphonates has been reported. This pratical and versatile three-component reaction involves the syn-addition of diphenyl H-phosphonate towards relatively inactive internal alkynes, as well as the concomitant transesterification of diphenyl H-phosphonate. The remarkable features include high stereoselectivity, wide substrate scope and the absence of additional ligands.

Key words: addition reaction, three-component reaction, vinylphosphonate, palladium, internal alkyne

引用此文

许振丽, 张宗雪, 孟晨湘, 张萧雅, 许凯, 刘澜涛, 王涛, 徐海云, 毛国梁. 无配体条件钯催化内炔的氢膦酰化反应合成(E)-烯烃膦酸酯类化合物[J]. 有机化学, 2021, 41(8): 3264-3271.

Zhenli Xu, Zongxue Zhang, Chenxiang Meng, Xiaoya Zhang, Kai Xu, Lantao Liu, Tao Wang, Haiyun Xu, Guoliang Mao. Ligand-Free Pd-Catalyzed Hydrophosphorylation of Internal Alkynes for the Synthesis of E-Vinylphosphonates[J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3264-3271.

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[1]	For reviews: see: pmid: 27787975
	(a) Moonen, K.; Laureyn, O.; Stevens, C. V. Chem. Rev. 2004, 104, 6177. doi: 10.1021/cr030451c pmid: 27787975
	(b) Demmer, C. S.; Larsen, N. K.; Bunch, L. Chem. Rev. 2011, 111, 7981. doi: 10.1021/cr2002646 pmid: 27787975
	(c) Queffelec, C.; Petit, M.; Janvier, P.; Knight, D. A.; Bujoli, B. Chem. Rev. 2012, 112, 3777. doi: 10.1021/cr2004212 pmid: 27787975
	(d) Galezowska, J.; Gumienna-Kontecka, E. Coord. Chem. Rev. 2012, 256, 105. doi: 10.1016/j.ccr.2011.07.002 pmid: 27787975
	(e) Soller, B. S.; Salzinger, S.; Rieger, B. Chem. Rev. 2016, 116, 1993. doi: 10.1021/acs.chemrev.5b00313 pmid: 27787975
	(f) Horsman, G. P.; Zechel, D. L. Chem. Rev. 2017, 117, 5704. doi: 10.1021/acs.chemrev.6b00536 pmid: 27787975
	(g) Shi, B. C.; Fang, Y. W.; Zhang, L.; Jin, X. P.; Wu, Y. H.; Fang, M.; Yang, Y. F.; Chen, C. Chin. J. Org. Chem. 2016, 36, 673. (in Chinese) pmid: 27787975
	(方烨汶, 张莉, 金小平, 武永辉, 方媚, 杨宇飞, 陈冲, 有机化学, 2016, 36, 673.) pmid: 27787975
	(h) Ye, X. Y.; Peng, L.; Bao, X. Z.; Tan, C. H.; Wang, H. Green Synth. Catal. 2021, 2, 6. pmid: 27787975
[2]	(a) Michaelis, A.; Kaehne, R. Ber. Dtsch. Chem. Ges. 1898, 31, 1048. doi: 10.1002/(ISSN)1099-0682 pmid: 28686460
	(b) Arbuzov, A. E. J. Russ. Phys. Chem. Soc. 1906, 38, 687. pmid: 28686460
	(c) Hirao, T.; Masunaga, T.; Ohshiro, Y.; Agawa, T. Tetrahedron Lett. 1980, 21, 3595. doi: 10.1016/0040-4039(80)80245-0 pmid: 28686460
	(d) Bhattacharya, A. K.; Thyagarajan, G. Chem. Rev. 1981, 81, 415. doi: 10.1021/cr00044a004 pmid: 28686460
	(e) Hirao, T.; Masunaga, T.; Yamada, N.; Ohshiro, Y.; Agawa, T. Bull. Chem. Soc. Jpn. 1982, 55, 909. doi: 10.1246/bcsj.55.909 pmid: 28686460
	(f) Russell, G. A.; Yao, C. F. J. Org. Chem. 1992, 57, 6508. doi: 10.1021/jo00050a026 pmid: 28686460
	(g) Zhong, P.; Huang, X.; Xiong, Z. X. Synlett 1999, 721. pmid: 28686460
	(h) Zhong, P.; Xiong, Z. X.; Huang, X. Synth. Commun. 2000, 30, 273. doi: 10.1080/00397910008087318 pmid: 28686460
	(i) Kabalka, G. K.; Guchhait, S. K. Org. Lett. 2003, 5, 729. pmid: 28686460
	(j) Thielges, S.; Bisseret, P.; Eustache, J. Org. Lett. 2005, 7, 681. pmid: 28686460
	(k) Zhuang, R. Q.; Xu, J.; Cai, Z. S.; Tang, G.; Fang, M. J.; Zhao, Y. F. Org. Lett. 2011, 13, 2110. doi: 10.1021/ol200465z pmid: 28686460
	(l) Evano, G.; Tadiparthi, K.; Couty, F. Chem. Commun. 2011, 47, 179. doi: 10.1039/C0CC01617A pmid: 28686460
	(m) Liu, L.; wang, Y. L.; Zeng, Z. P.; Xu, P. X.; Gao, Y. X.; Yin, Y. W.; Zhao, Y. F. Adv. Synth. Catal. 2013, 355, 659. doi: 10.1002/adsc.201200853 pmid: 28686460
	(n) Wu, Y. L.; Liu, L. L.; Yan, K. L.; Xu, P. X.; Gao, Y. X.; Zhao, Y. F. J. Org. Chem. 2014, 79, 8118. doi: 10.1021/jo501321m pmid: 28686460
	(o) Liu, L.; Lv, Y.; Wu, Y. L.; gao, X.; Zeng, Z. P.; Gao, Y. X.; Tang, G.; Zhao, Y. F. RSC Adv. 2014, 4, 2322. doi: 10.1039/C3RA45212C pmid: 28686460
	(p) Gui, Q. W.; Hu, L.; Chen, X.; Liu, J. D.; Tan, Z. Chem. Commun. 2015, 51, 13922. doi: 10.1039/C5CC04826E pmid: 28686460
	(q) Xue, J. F.; Zhou, S. F.; Liu, Y. Y.; Pan, X. Q.; Zou, J. P.; Asekun, O. T. Org. Biomol. Chem. 2015, 13, 4896. doi: 10.1039/C5OB00404G pmid: 28686460
	(r) Yuan, J. W.; Yang, L. R.; Mao, P.; Qu, L. B. RSC Adv. 2016, 6, 87058. doi: 10.1039/C6RA19002B pmid: 28686460
	(s) Liaom, L. L.; Gui, Y. Y.; Zhang, X. B.; Shen, G.; Liu, H. D.; Zhou, W. J.; Li, J.; Yu, D. G. Org. Lett. 2017, 19, 3735. doi: 10.1021/acs.orglett.7b01561 pmid: 28686460
	(t) Gu, J.; Cai, C. Org. Biomol. Chem. 2017, 15, 4226. doi: 10.1039/C7OB00505A pmid: 28686460
	(u) Liu, L. X.; Zhou, D.; Dong, J. Y.; Zhou, Y. B.; Yin, S. F.; Han, L. B. J. Org. Chem. 2018, 83, 4190. doi: 10.1021/acs.joc.8b00187 pmid: 28686460
	(v) Wang, L.; Yang, Z.; Zhu, H. J.; Liu, H. T.; Lv, S. P.; Xu, Y. Eur. J. Org. Chem. 2019, 2019, 2138. doi: 10.1002/ejoc.201801678 pmid: 28686460
	(w) Ghasemzadeh, M. S.; Akhlaghinia, B. New J. Chem. 2019, 43, 5341. doi: 10.1039/c9nj00352e pmid: 28686460
	(x) Liu, C. W.; Ji, C. L.; Zhou, T. L.; Hong, X.; Szostak, M. Org. Lett. 2019, 21, 9256. doi: 10.1021/acs.orglett.9b03678 pmid: 28686460
	(y) Qiao, B. K.; Cao, H. Q.; Huang, Y. J.; Zhang, Y.; Nie, J.; Zhang, F. G.; Ma, J. A. Chin. J. Chem. 2018, 36, 809. doi: 10.1002/cjoc.v36.9 pmid: 28686460
	(z) Ren, L. J.; Ran, M. G.; Fang, X. H.; Zhao, L.; Yao, Q. L. Chin. J. Org. Chem. 2018, 38, 2791. (in Chinese) doi: 10.6023/cjoc201803016 pmid: 28686460
	(任林静, 冉茂刚, 方学红, 赵玲, 姚秋丽, 有机化学, 2018, 38, 2791.) doi: 10.6023/cjoc201803016 pmid: 28686460
[3]	(a) Han, L. B.; Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571. doi: 10.1021/ja953690t
	(b) Han, L. B.; Hua, R. M.; Tanaka, M. Angew. Chem. Int. Ed. 1998, 37, 94.
	(c) Lai, C. B.; Xi, C. J.; Chen, C.; Ma, M. M.; Hong, X. Y. Chem. Commun. 2003, 2736.
	(d) Trostyanskaya, I. G.; Beletskaya, I. P. Tetrahedron 2005, 61, 6315. doi: 10.1016/j.tet.2005.03.107
	(e) Ananikov, V. P.; Khemchyan, L. L.; Beletskaya, I. P. Russ. J. Org. Chem. 2010, 46, 1269. doi: 10.1134/S1070428010090010
	(f) Ananikov, V. P.; Khemchyan, L. L.; Beletskaya, I. P.; Starikova, Z. A. Adv. Synth. Catal. 2010, 352, 2979. doi: 10.1002/adsc.v352.17
	(g) Xu, Q.; Shen, R. W.; Ono, Y.; Nagahata, R.; Shimada, S.; Goto, M.; Han, L. B. Chem. Commun. 2011, 47, 2333. doi: 10.1039/C0CC03436C
	(h) Khemchyan, L. L.; Ivanova, J. V.; Zalesskiy, S. S.; Ananikov, V. P.; Beletskaya, I. P.; Starikova, Z. A. Adv. Synth. Catal. 2014, 356, 771. doi: 10.1002/adsc.v356.4
	(i) Islas, R. E.; García, J. J. ChemCatChem 2017, 9, 4125. doi: 10.1002/cctc.v9.21
	(j) Chen, T. Q.; Zhao, C. Q.; Han, L. B. J. Am. Chem. Soc. 2018, 140, 3139. doi: 10.1021/jacs.8b00550
	(k) Wei, X. H.; Bai, C. Y.; Zhao, L. B.; Zhang, P.; Li, Z. H.; Wang, Y. B.; Su, Q. Chin. J. Chem. 2021, 39, 1855. doi: 10.1002/cjoc.v39.7
[4]	Kers, A.; Kers, I.; Stawinski, J.; Sobkowski, M.; Kraszewski, A. Synthesis 1995, 427.
[5]	(a) Huang, H.; Denne, J.; Yang, C. H.; Wang, H. B.; Kang, J. Y. Angew. Chem. Int. Ed. 2018, 57, 6624. doi: 10.1002/anie.v57.22
	(b) Adler, P.; Pons, A.; Li, J.; Heider, J.; Brutiu, B. R.; Maulide, N. Angew. Chem. Int. Ed. 2018, 57, 13330. doi: 10.1002/anie.v57.40
[6]	(a) Xu, K.; Hu, H.; Yang, F.; Wu, Y. J. Eur. J. Org. Chem. 2013, 2013, 319.
	(b) Xu, K.; Yang, F.; Zhang, G. D.; Wu, Y. J. Green Chem. 2013, 15, 1055. doi: 10.1039/c3gc00030c
[7]	Ouyang, K. B.; Xi, Z. F. Acta Chim. Sinica 2013, 71, 13. doi: 10.6023/A12110984
[8]	Park, K.; Bae, G.; Moon, J.; Choe, J.; Song, K.; Lee, S. J. Org. Chem. 2010, 75, 6244 doi: 10.1021/jo101398a
[9]	Kobayashi, Y.; William, A. D. Adv. Synth. Catal. 2004, 346, 1749. doi: 10.1002/adsc.200404191

Entry	Catalyst	Base	Additive	Solvent	Yield^b/%
1	Pd(OAc)₂	KOH	No	EtOH	43
2	Pd(OAc)₂	K₂CO₃	No	EtOH	18
3	Pd(OAc)₂	K₃PO₄	No	EtOH	63
4	Pd(OAc)₂	KF	No	EtOH	67
5	Pd(OAc)₂	Pyridine	No	EtOH	<5
6	Pd(OAc)₂	NEt₃	No	EtOH	68
7	Pd(OAc)₂	ⁿBu₃N	No	EtOH	85
8^c	Pd(OAc)₂	ⁿBu₃N	No	EtOH	78
9	PdCl₂	ⁿBu₃N	No	EtOH	43
10	NiCl₂	ⁿBu₃N	No	EtOH	<5
11	Pd(OAc)₂	ⁿBu₃N	No	ⁱPrOH	17
12	Pd(OAc)₂	DBU	No	ⁱPrOH	<5
13	Pd(OAc)₂	KOH	No	ⁱPrOH	67
14	Pd(OAc)₂	K₂CO₃	No	ⁱPrOH	79
15	Pd(OAc)₂	KOAc	No	ⁱPrOH	48
16	Pd(OAc)₂	K₃PO₄	No	ⁱPrOH	64
17	Pd(OAc)₂	KF	No	ⁱPrOH	66
18	PdCl₂	K₂CO₃	No	ⁱPrOH	24
19	NiCl₂	K₂CO₃	No	ⁱPrOH	<5
20	Pd(OAc)₂	K₂CO₃	TBAB	ⁱPrOH	83

Entry	Catalyst	Base	Additive	Solvent	Yield^b/%
1	Pd(OAc)₂	KOH	No	EtOH	43
2	Pd(OAc)₂	K₂CO₃	No	EtOH	18
3	Pd(OAc)₂	K₃PO₄	No	EtOH	63
4	Pd(OAc)₂	KF	No	EtOH	67
5	Pd(OAc)₂	Pyridine	No	EtOH	<5
6	Pd(OAc)₂	NEt₃	No	EtOH	68
7	Pd(OAc)₂	ⁿBu₃N	No	EtOH	85
8^c	Pd(OAc)₂	ⁿBu₃N	No	EtOH	78
9	PdCl₂	ⁿBu₃N	No	EtOH	43
10	NiCl₂	ⁿBu₃N	No	EtOH	<5
11	Pd(OAc)₂	ⁿBu₃N	No	ⁱPrOH	17
12	Pd(OAc)₂	DBU	No	ⁱPrOH	<5
13	Pd(OAc)₂	KOH	No	ⁱPrOH	67
14	Pd(OAc)₂	K₂CO₃	No	ⁱPrOH	79
15	Pd(OAc)₂	KOAc	No	ⁱPrOH	48
16	Pd(OAc)₂	K₃PO₄	No	ⁱPrOH	64
17	Pd(OAc)₂	KF	No	ⁱPrOH	66
18	PdCl₂	K₂CO₃	No	ⁱPrOH	24
19	NiCl₂	K₂CO₃	No	ⁱPrOH	<5
20	Pd(OAc)₂	K₂CO₃	TBAB	ⁱPrOH	83

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无配体条件钯催化内炔的氢膦酰化反应合成(E)-烯烃膦酸酯类化合物

Ligand-Free Pd-Catalyzed Hydrophosphorylation of Internal Alkynes for the Synthesis of E-Vinylphosphonates

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