Direct Nucleophilic Substitution of Propargyl Alcohols with Enoxysilanes

doi:10.6023/cjoc202007011

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (1): 407-411.DOI: 10.6023/cjoc202007011 Previous Articles Next Articles

Special Issue: 有机硅化学虚拟合辑

NOTES

炔丙醇与烯醇硅醚的直接亲核取代反应

李鑫玲^a, 刘会丽^a, 张顺吉^a^,^*()

a 淮北师范大学化学与材料科学学院安徽淮北 235000

收稿日期:2020-07-04 修回日期:2020-08-06 发布日期:2020-08-27
通讯作者: 张顺吉
作者简介:
* Corresponding authors. E-mail: sjzhang@chnu.edu.cn

Direct Nucleophilic Substitution of Propargyl Alcohols with Enoxysilanes

Xinling Li^a, Huili Liu^a, Shunji Zhang^a^,^*()

a Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000

Received:2020-07-04 Revised:2020-08-06 Published:2020-08-27
Contact: Shunji Zhang

1. cjoc202007011辅助材料.pdf(1004KB)

Abstract

A novel and efficient synthesis of γ-alkynyl ketones by the direct nucleophilic substitution of propargyl alcohols with enoxysilanes in the presence of a catalytic amount of p-toluenesulfonic acid monohydrate, has been developed. The reactions can be performed in an undried solvent under an air atmosphere to obtain the desired products in good yields.

Key words: Keywords propargyl alcohol, enoxysilane, nucleophilic substitution, catalyzed, p-toluenesulfonic acid

Cite this article

Xinling Li, Huili Liu, Shunji Zhang. Direct Nucleophilic Substitution of Propargyl Alcohols with Enoxysilanes[J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 407-411.

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Fig. & Tab. 1

References 11

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Entry	1	R ¹	R ²	2	R ³	R ⁴	t/℃	Product	Isolated yield/%
1	1a	Ph	Ph	2a	H	COOMe	60	3a	85
2	1b	4-ClC ₆H ₄	Ph	2a	H	COOMe	60	3b	82
3	1c	4-BrC ₆H ₄	Ph	2a	H	COOMe	60	3c	80
4	1d	2-MeO-5-BrC ₆H ₃	Ph	2a	H	COOMe	60	3d	78
5	1e	2-MeOC ₆H ₄	Ph	2a	H	COOMe	r.t.	3e	83
6	1f	4-BnOC ₆H ₄	Ph	2a	H	COOMe	r.t.	3f	90
7	1g	4-BnOC ₆H ₄	n-Pentyl	2a	H	COOMe	r.t.	3g	88
8	1h	2-Naphthyl	Ph	2a	H	COOMe	r.t.	3h	91
9	1i	4-MeO-3-FC ₆H ₃	Ph	2a	H	COOMe	r.t.	3i	88
10	1j	3,4-Me ₂C ₆H ₃	Ph	2a	H	COOMe	r.t.	3j	92
11	1k	3,4-(MeO) ₂C ₆H ₃	Ph	2a	H	COOMe	r.t.	3k	95
12	1l	n-Bu	Ph	2a	H	COOMe	r.t.	—	0
13	1k	3,4-(MeO) ₂C ₆H ₃	Ph	2b	—(CH ₂) ₄—		r.t.	3l	93
14	1f	4-BnOC ₆H ₄	Ph	2b	—(CH ₂) ₄—		r.t.	3m	95
15	1k	3,4-(MeO) ₂C ₆H ₃	Ph	2c	H	Me	r.t.	3n	79
16	1k	3,4-(MeO) ₂C ₆H ₃	Ph	2d	H	Ph	r.t.	3o	85

Entry	1	R ¹	R ²	2	R ³	R ⁴	t/℃	Product	Isolated yield/%
1	1a	Ph	Ph	2a	H	COOMe	60	3a	85
2	1b	4-ClC ₆H ₄	Ph	2a	H	COOMe	60	3b	82
3	1c	4-BrC ₆H ₄	Ph	2a	H	COOMe	60	3c	80
4	1d	2-MeO-5-BrC ₆H ₃	Ph	2a	H	COOMe	60	3d	78
5	1e	2-MeOC ₆H ₄	Ph	2a	H	COOMe	r.t.	3e	83
6	1f	4-BnOC ₆H ₄	Ph	2a	H	COOMe	r.t.	3f	90
7	1g	4-BnOC ₆H ₄	n-Pentyl	2a	H	COOMe	r.t.	3g	88
8	1h	2-Naphthyl	Ph	2a	H	COOMe	r.t.	3h	91
9	1i	4-MeO-3-FC ₆H ₃	Ph	2a	H	COOMe	r.t.	3i	88
10	1j	3,4-Me ₂C ₆H ₃	Ph	2a	H	COOMe	r.t.	3j	92
11	1k	3,4-(MeO) ₂C ₆H ₃	Ph	2a	H	COOMe	r.t.	3k	95
12	1l	n-Bu	Ph	2a	H	COOMe	r.t.	—	0
13	1k	3,4-(MeO) ₂C ₆H ₃	Ph	2b	—(CH ₂) ₄—		r.t.	3l	93
14	1f	4-BnOC ₆H ₄	Ph	2b	—(CH ₂) ₄—		r.t.	3m	95
15	1k	3,4-(MeO) ₂C ₆H ₃	Ph	2c	H	Me	r.t.	3n	79
16	1k	3,4-(MeO) ₂C ₆H ₃	Ph	2d	H	Ph	r.t.	3o	85

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炔丙醇与烯醇硅醚的直接亲核取代反应

Direct Nucleophilic Substitution of Propargyl Alcohols with Enoxysilanes

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