Palladium-Catalyzed Stereoselective 1,3-Diarylation of 1,4-Cyclohexadiene

doi:10.6023/cjoc202006022

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (2): 849-856.DOI: 10.6023/cjoc202006022 Previous Articles Next Articles

NOTE

钯催化的1,4-环己二烯的立体选择性1,3-双芳基化反应

庞海亮¹, 吴冬¹, 阴国印¹^,^*()

1 武汉大学高等研究院武汉 430072

收稿日期:2020-06-12 修回日期:2020-08-28 发布日期:2020-09-16
通讯作者: 阴国印
作者简介:
* Corresponding author. E-mail: yinguoyin@whu.edu.cn
基金资助:
国家自然科学基金(21702151); 国家自然科学基金(21871211); 中央大学基础研究基金(2042019kf0208)

Palladium-Catalyzed Stereoselective 1,3-Diarylation of 1,4-Cyclohexadiene

Hailiang Pang¹, Dong Wu¹, Guoyin Yin¹^,^*()

1 Institute for Advanced Studies, Wuhan University, Wuhan 430072

Received:2020-06-12 Revised:2020-08-28 Published:2020-09-16
Contact: Guoyin Yin
Supported by:
the National Natural Science Foundation of China(21702151); the National Natural Science Foundation of China(21871211); the Fundamental Research Funds for Central Universities(2042019kf0208)

1. cjoc202006022.pdf(3772KB)

Abstract

A palladium-catalyzed migratory diarylation of unconjugated cyclohexadiene is disclosed, which exihibits high 1,3-regioselectivity and exclusive cis-diastereoselectivity. The excellent selectivity suggests that the olefin does not dissocate from the palladium during chain-walking. This study provides a simple method for the synthesis of 1,3-diaryl-substituted cyclohexanes

Key words: palladium catalysis, metal migration, alkene, stereoselectivity

Cite this article

Hailiang Pang, Dong Wu, Guoyin Yin. Palladium-Catalyzed Stereoselective 1,3-Diarylation of 1,4-Cyclohexadiene[J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 849-856.

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Fig. & Tab. 7

References 9

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Entry	Base	Additive	Solvent	Yield^b/%
1	CsF	Me₄NCl	DMF	47
2	CsF	n-Bu₄NCl	DMF	38
3	CsF	n-Bu₄NBr	DMF	30
4	CsF	Et₄NBr	DMF	35
5	CsF	LiCl	DMF	12
6	CsF	MgCl₂	DMF	Trace
7	CsF	—	DMF	23
8	CsF	Me₄NCl	NMP	60
9	CsF	Me₄NCl	DMA	68
10	CsF	Me₄NCl	CH₃CN	28
11	CsF	Me₄NCl	DME	33
12	CsF	Me₄NCl	Dioxane	44
13	CsF	Me₄NCl	CHCl₃	20
14	CsF	Me₄NCl	DCE	73
15	KF	Me₄NCl	DCE	5
16	Na₂CO₃	Me₄NCl	DCE	37
17	K₂CO₃	Me₄NCl	DCE	67
18	K₃PO₄	Me₄NCl	DCE	31
19^c	CsF	Me₄NCl	DCE	37
20^d	CsF	Me₄NCl	DCE	81 (79) ^e

Entry	Base	Additive	Solvent	Yield^b/%
1	CsF	Me₄NCl	DMF	47
2	CsF	n-Bu₄NCl	DMF	38
3	CsF	n-Bu₄NBr	DMF	30
4	CsF	Et₄NBr	DMF	35
5	CsF	LiCl	DMF	12
6	CsF	MgCl₂	DMF	Trace
7	CsF	—	DMF	23
8	CsF	Me₄NCl	NMP	60
9	CsF	Me₄NCl	DMA	68
10	CsF	Me₄NCl	CH₃CN	28
11	CsF	Me₄NCl	DME	33
12	CsF	Me₄NCl	Dioxane	44
13	CsF	Me₄NCl	CHCl₃	20
14	CsF	Me₄NCl	DCE	73
15	KF	Me₄NCl	DCE	5
16	Na₂CO₃	Me₄NCl	DCE	37
17	K₂CO₃	Me₄NCl	DCE	67
18	K₃PO₄	Me₄NCl	DCE	31
19^c	CsF	Me₄NCl	DCE	37
20^d	CsF	Me₄NCl	DCE	81 (79) ^e

Entry	Base	Solvent	Yield^b/%	Entry	Base	Solvent	Yield^b/%
1	Et₃N	DCE	0	12	LiOMe	DCE	34
2	KF	DCE	0	13	NaOMe	DCE	0
3	NaOAc	DCE	0	14	LiOMe	DMF	0
4	NaHCO₃	DCE	Trace	15	LiOMe	CHCl₃	39
5	Cs₂CO₃	DCE	14	16	LiOMe	DME	4
6	K₂CO₃	DCE	23	17	LiOMe	Dioxane	49
7	LiOH	DCE	10	18	LiOMe	THF	7
8	NaOH	DCE	0	19^c	LiOMe	Dioxane	20
9	KOH	DCE	0	20^d	LiOMe	Dioxane	75^f
10	K₃PO₃	DCE	0	21^e	LiOMe	Dioxane	Trace
11	LiO^tBu	DCE	27

Entry	Base	Solvent	Yield^b/%	Entry	Base	Solvent	Yield^b/%
1	Et₃N	DCE	0	12	LiOMe	DCE	34
2	KF	DCE	0	13	NaOMe	DCE	0
3	NaOAc	DCE	0	14	LiOMe	DMF	0
4	NaHCO₃	DCE	Trace	15	LiOMe	CHCl₃	39
5	Cs₂CO₃	DCE	14	16	LiOMe	DME	4
6	K₂CO₃	DCE	23	17	LiOMe	Dioxane	49
7	LiOH	DCE	10	18	LiOMe	THF	7
8	NaOH	DCE	0	19^c	LiOMe	Dioxane	20
9	KOH	DCE	0	20^d	LiOMe	Dioxane	75^f
10	K₃PO₃	DCE	0	21^e	LiOMe	Dioxane	Trace
11	LiO^tBu	DCE	27

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钯催化的1,4-环己二烯的立体选择性1,3-双芳基化反应

Palladium-Catalyzed Stereoselective 1,3-Diarylation of 1,4-Cyclohexadiene

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