A Novel Method for the Synthesis Triarylphosphines under Transition-Metal-Free Conditions

doi:10.6023/cjoc201904006

Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (10): 2930-2935.DOI: 10.6023/cjoc201904006 Previous Articles Next Articles

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无过渡金属参与的三芳基膦化合物合成新方法研究

尹清, 于晓强^*(), 包明

大连理工大学精细化工国家重点实验室大连 116024

收稿日期:2019-04-02 修回日期:2019-04-26 发布日期:2019-05-21
通讯作者: 于晓强 E-mail:yuxiaoqiang@dlut.edu.cn
基金资助:
国家自然科学基金(Nos. 21572028);国家自然科学基金(21573032)

A Novel Method for the Synthesis Triarylphosphines under Transition-Metal-Free Conditions

Yin, Qing, Yu, Xiaoqiang^*(), Bao, Ming

State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024

Received:2019-04-02 Revised:2019-04-26 Published:2019-05-21
Contact: Yu, Xiaoqiang E-mail:yuxiaoqiang@dlut.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China(Nos. 21572028);Project supported by the National Natural Science Foundation of China(21573032)

Triarylphosphines play an important role in pharmaceutical synthesis and transition-meal-catalyzed reactions. In this paper, a novel method for the synthesis of triarylphosphines via base-promoted C(sp ²)—P cross-coupling reactions of alkyldiphenylphosphines with aryl halides is described. The transition-metal-free reaction condition, readily available starting materials and experimental simplicity are the features of the novel method.

Key words: transition metal-free, alkyldiphenylphosphines, aryl halides, triarylphosphines

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Yin, Qing, Yu, Xiaoqiang, Bao, Ming. A Novel Method for the Synthesis Triarylphosphines under Transition-Metal-Free Conditions[J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2930-2935.

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Fig. & Tab. 5

References 14

[1]	(a) Martin, R.; Buchwald, S. L. Acc. Chem. Res. 2008, 41, 1461.
	(b) Beletskaya, I. P.; Kazankova, M. A. Russ. J. Org. Chem. 2002, 38, 1391.
	(c) Kosolapoff, G. M.; Maier, L. In Organic Phosphorus Compounds, Vol. 1, 2nd ed., Wiley-Interscience, New York, 1972, p. 545.
	(d) Ojima, I.; Clos, N.; Bastos, C. Tetrahedron 1989, 45, 6901.
	(e) Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 6338.
[2]	(a) Tran, U. P. N.; Hock, K, J.; Gordon, C. P. Chem. Commun. 2017, 53, 4950.
	(b) Zheng, F.; Leung, T.; Chan, K. Chem. Commun. 2016, 52, 10767.
	(c) Shih, H. W.; Prescher, J. A. J. Am. Chem. Soc. 2015, 137, 10036.
[3]	(a) Jiménez, M. V.; Pérez-Torrente, J. J . Synjournal 2009,1916.
	(b) Zakharkin, L. I.; Anikina, E. V. Izv. Akad. Nauk SSSR, Ser. Khim. 1990, 3, 714.
	(c) Unruh, J. D.; Christenson, J. R . J. Mol. Catal. 1982, 14 19..
	(d) Imamoto, T.; Kikuchi, S. I.; Miura, T.; Wada, Y . Org. Lett. 2001, 3 87.
[4]	(a) Michaelis, A. Chem. Ber. 1879, 12, 1009.
	(b) Kosolapoff, G. M.; Huber, W. F. J. Am. Chem. Soc. 1947, 69, 2020.
	(c) Gefter, E. L. Zh. Obsh. Khim. 1958, 28, 1338.
[5]	(a) Li, Y.; Das, S.; Beller, M. J. Am. Chem. Soc. 2012, 134, 9727.
	(b) Buonomo, J. A.; Eiden, C. G.; Aldrich, C. C. Chem.-Eur. J. 2017, 23, 14434.
	(c) Herault, D.; Nguyen, D. H.; Nuel, D . Chem. Soc. Rev. 2015, 44 2508..
	(d) Rinehart, N. I.; Kendall, A. J.; Tyler, D. R . Organometallics 2018, 37 182..
	(e) Tunney, S. E.; Stille, J. K . J. Org. Chem. 1987, 52 748.
[6]	(a) Herd, O.; Stelzer, O. J. Organomet. Chem. 1996, 522, 69.
	(b) Machnitzki, P.; Stelzer, O. Eur. J. Inorg. Chem. 1998, 7, 1029.
	(c) Nowrouzi, N.; Keshtgar, S.; Jahromi, E. B . Tetrahedron Lett. 2016, 57 348..
	(d) Xu, Z.; Wang, P.; Cai, M . J. Org. Chem. 2018, 866 50..
	(e) Stadler, A.; Kappe, C. O . Org. Lett. 2002, 4 3541..
	(f) Lian, Z.; Bhawal, B. N.; Yu, P.; Morandi, B . Science 2017, 356 1059.
[7]	(a) Yang, J.; Chen, T.; Han, L. B. J. Am. Chem. Soc. 2015, 137, 1782.
	(b) Cai, D.; Payack, J. F.; Bender, D. R.; Hughes, D. L. J. Org. Chem. 1994, 59, 7180.
	(c) Cai, D.; Payack, J. F.; Bender, D. R . Org. Synth. 1998, 76 6..
	(d) Sun, M.; Zang, Y. S.; Hou, L. K . Eur. J. Org. Chem. 2014, 30 6796.
[8]	(a) Fang, Z.; Cai, M.; Lin, Y.; Zhao, H. Appl. Organomet. Chem. 2018, 32, 4417.
	(b) Allen, D. V.; Venkataraman, D. J. Org. Chem. 2003, 68, 4590.
	(c) Gelman, D.; Jiang, L.; Buchwald, S. L . Org. Lett. 2003, 5 2315..
	(d) Rao, H. H.; Jin, Y.; Zhao, Y. F . Chem.- Eur. J. 2006, 12 3636..
	(e) Huang, C.; Tang, X.; Jiang, Y. Y.; Zhao, Y. F . J. Org. Chem. 2006, 71 5020.
[9]	(a) Li, Y.; Chakrabarty, S.; Studer, A. Angew. Chem., Int. Ed. 2016, 55, 802.
	(b) Schumann, H.; Jutzi, P.; Schmidt, M. Angew. Chem., Int. Ed. Engl. 1965, 4, 869.
	(c) Schumann, H.; Jutzi, P.; Schmidt, M . Angew. Chem. 1965, 77 912.
[10]	Li, Y. M.; Yang, S. D . Synthesis 2013,1739.
[11]	(a) Yu, R. R.; Chen, X. Y.; Martin, S. F.; Wang, Z. Q. Org. Lett. 2017, 19, 1808.
	(b) Yu, R. R.; Chen, X. Y.; Wang, Z. Q. Tetranedron Lett. 2016, 57, 3404.
	(c) Yang, J. F.; Wu, H. Y.; Wang, Z. Q.; Saudi, J . Chem. Soc. 2016, 7 1319.
[12]	Nandi, P.; Dye, J. L.; Bentley, P.; Jackson, J. E. Org. Lett. 2009, 11, 1689.
[13]	(a) Shirakawa, E.; Zhang, X.; Hayashi, T. Angew. Chem. Int. Ed. 2011, 50, 4671.
	(b) Bunnett, J. F. Acc. Chem. Res. 1978, 11, 413.
[14]	Schindlbauer, H . Monatsh. Chem. 1965, 96. 2058. doi: 10.1007/BF01185936

Entry	Base	Solvent	Yield^b/%
1	Cs₂CO₃	DMSO	39
2	K₂CO₃	DMSO	NR^c
3	KOAc	DMSO	NR^c
4	K₃PO₄	DMSO	45
5	^tBuONa	DMSO	50
6	^tBuOK	DMSO	70
7	Pyridine	DMSO	23
8	Et₃N	DMSO	42
9	TMEDA	DMSO	29
10	2,2'-bpy	DMSO	30
11	^tBuOK	DMF	Trace
12	^tBuOK	DMAc	33
13	^tBuOK	NMP	Trace
14	^tBuOK	HMPA	NR^c
15	^tBuOK	Tolune	NR^c
16	^tBuOK	1,4-Dioxane	NR^c

Entry	Base	Solvent	Yield^b/%
1	Cs₂CO₃	DMSO	39
2	K₂CO₃	DMSO	NR^c
3	KOAc	DMSO	NR^c
4	K₃PO₄	DMSO	45
5	^tBuONa	DMSO	50
6	^tBuOK	DMSO	70
7	Pyridine	DMSO	23
8	Et₃N	DMSO	42
9	TMEDA	DMSO	29
10	2,2'-bpy	DMSO	30
11	^tBuOK	DMF	Trace
12	^tBuOK	DMAc	33
13	^tBuOK	NMP	Trace
14	^tBuOK	HMPA	NR^c
15	^tBuOK	Tolune	NR^c
16	^tBuOK	1,4-Dioxane	NR^c

Entry	Aryl halide 2	Product 3	Yield^b/%	Entry	Aryl halide 2	Product 3	Yield^b/%
1	2a	3a	46	7	2a	3a	44
2	2b	3b	53	8	2b	3b	47
3	2c	3c	40	9	2c	3c	40
4	2a	3a	36	10	2a	—	NR^c
5	2b	3b	40	11	2b	—	NR^c
6	2c	3c	30	12	2c	—	NR^c

Entry	Aryl halide 2	Product 3	Yield^b/%	Entry	Aryl halide 2	Product 3	Yield^b/%
1	2a	3a	46	7	2a	3a	44
2	2b	3b	53	8	2b	3b	47
3	2c	3c	40	9	2c	3c	40
4	2a	3a	36	10	2a	—	NR^c
5	2b	3b	40	11	2b	—	NR^c
6	2c	3c	30	12	2c	—	NR^c

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无过渡金属参与的三芳基膦化合物合成新方法研究

A Novel Method for the Synthesis Triarylphosphines under Transition-Metal-Free Conditions

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