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

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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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