Research of Visible Light/Lewis Base Dual Catalytic Defluorinative Silylation of Trifluoromethyl-Substituted Alkenes

doi:10.6023/cjoc202304034

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (10): 3623-3634.DOI: 10.6023/cjoc202304034 Previous Articles Next Articles

Special Issue: 有机氟化学虚拟合辑；有机硅化学专辑-2023

可见光/路易斯碱协同催化的三氟甲基取代烯烃脱氟硅化反应研究

朱佳洁, 万义, 袁启洋, 魏金莲^*(), 张永强^*()

华东理工大学药学院上海 200237

收稿日期:2023-05-02 修回日期:2023-06-30 发布日期:2023-07-19
基金资助:
国家自然科学基金(22171080); 上海市自然科学基金(23ZR1417200)

Research of Visible Light/Lewis Base Dual Catalytic Defluorinative Silylation of Trifluoromethyl-Substituted Alkenes

Jiajie Zhu, Yi Wan, Qiyang Yuan, Jinlian Wei(), Yongqiang Zhang()

School of Pharmacy, East China University of Science and Technology, Shanghai 200237

Received:2023-05-02 Revised:2023-06-30 Published:2023-07-19
Contact: *E-mail: yongqiangzhang@ecust.edu.cn; weijinlian678@ecust.edu.cn
Supported by:
National Natural Science Foundation of China(22171080); Natural Science Foundation of Shanghai(23ZR1417200)

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Abstract

A novel photoredox/Lewis base dual-catalytic defluorinative silylation reaction of trifluoromethylsubstituted alkenes for the synthesis of gem-difluoroallylsilanes is reported, where silylboranes are employed as the silyl donor reagents. The protocol proceeds via the catalytic activation of Si—B bond by a Lewis base quinuclidine and the formation of silyl radical, making it easy to scale up. It features mild and green reaction conditions, simple reaction system, broad substrate scope and good functional group compatibility. Furthermore, the potential of this class of building blocks in the construction of various gem-difluoromethyl-containing structures has been also demostrated.

Key words: visible light catalysis, Lewis base catalysis, silylboranes, trifluoromethyl-substituted alkenes, synthesis of gem- difluoroallylsilanes

Cite this article

Jiajie Zhu, Yi Wan, Qiyang Yuan, Jinlian Wei, Yongqiang Zhang. Research of Visible Light/Lewis Base Dual Catalytic Defluorinative Silylation of Trifluoromethyl-Substituted Alkenes[J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3623-3634.

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Entry	Photocat.	Lewis base cat.	Yield^b/% of 3a	3a/3a' ^c
1	P1	Quinuclidine	60^d	10∶1
2	P1	Quinuclidine	90	>50∶1
3	P1	DMAP	80	>50∶1
4	P1	Triphenylphosphine	54	>50∶1
5	P1	Quinuclidine	66^e	>50∶1
6	P1	—	11	—
7	P2	Quinuclidine	34	20∶1
8	P3	Quinuclidine	N.d.^f^,^g	—
9	P4	Quinuclidine	86	>50∶1
10	P5	Quinuclidine	86^g	>50∶1
11	—	Quinuclidine	Trace	—
12	P1	Quinuclidine	Trace^h	—
13	P1	Quinuclidine	53ⁱ	>50∶1
14	P1	Quinuclidine	Trace^j	—

Entry	Photocat.	Lewis base cat.	Yield^b/% of 3a	3a/3a' ^c
1	P1	Quinuclidine	60^d	10∶1
2	P1	Quinuclidine	90	>50∶1
3	P1	DMAP	80	>50∶1
4	P1	Triphenylphosphine	54	>50∶1
5	P1	Quinuclidine	66^e	>50∶1
6	P1	—	11	—
7	P2	Quinuclidine	34	20∶1
8	P3	Quinuclidine	N.d.^f^,^g	—
9	P4	Quinuclidine	86	>50∶1
10	P5	Quinuclidine	86^g	>50∶1
11	—	Quinuclidine	Trace	—
12	P1	Quinuclidine	Trace^h	—
13	P1	Quinuclidine	53ⁱ	>50∶1
14	P1	Quinuclidine	Trace^j	—

可见光/路易斯碱协同催化的三氟甲基取代烯烃脱氟硅化反应研究

Research of Visible Light/Lewis Base Dual Catalytic Defluorinative Silylation of Trifluoromethyl-Substituted Alkenes

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