Nickel-Catalyzed [4＋2] Cyclization of Benzosilacyclobutenes and Acylsilanes

doi:10.6023/cjoc202304035

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (10): 3635-3643.DOI: 10.6023/cjoc202304035 Previous Articles Next Articles

Special Issue: 有机硅化学专辑-2023

镍催化苯并硅杂环丁烷与酰基硅烷的[4＋2]环化反应

张维露^a^,^b, 陈绍维^a^,^b, 沈晓^a^,^b^,^*()

a 武汉大学高等研究院武汉 430072
b 有机硅化合物及材料教育部工程研究中心武汉 430072

收稿日期:2023-04-28 修回日期:2023-06-24 发布日期:2023-07-12
基金资助:
国家重点研究发展计划(2022YFA1506100); 中央高校基本科研基金(2042023kf1010); 中央高校基本科研基金(2042023kf0202); 国家自然科学基金(21901191)

Nickel-Catalyzed [4＋2] Cyclization of Benzosilacyclobutenes and Acylsilanes

Weilu Zhang^a^,^b, Shaowei Chen^a^,^b, Xiao Shen^a^,^b()

a Institute for Advanced Studies, Wuhan University, Wuhan 430072
b Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, Wuhan 430072

Received:2023-04-28 Revised:2023-06-24 Published:2023-07-12
Contact: *E-mail: xiaoshen@whu.edu.cn
Supported by:
National Key R&D Program of China(2022YFA1506100); Fundamental Research Funds for the Central Universities(2042023kf1010); Fundamental Research Funds for the Central Universities(2042023kf0202); National Natural Science Foundation of China(21901191)

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Abstract

A nickel-catalyzed [4＋2] cyclization reaction between benzosilacyclobutenes and acylsilanes for the synthesis of cyclic bissilanes is reported. The mild reaction showes good substrate scope and the products can be transformed to monoaclohols or diols via one-step down-stream transformations.

Key words: nickel catalysis, benzosilacyclobutene, acylsilane, cycloaddition, C—Si bond activation

Cite this article

Weilu Zhang, Shaowei Chen, Xiao Shen. Nickel-Catalyzed [4＋2] Cyclization of Benzosilacyclobutenes and Acylsilanes[J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3635-3643.

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References 10

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Entry	Ligand	1a/2a	Solvent	T/℃	Yield/%
1	DPPM	1∶1	Toluene	100	<5
2	P(p-MeC₆H₄)₃	1∶1	Toluene	100	32
3	P(ⁿBu)Ad₂	1∶1	Toluene	100	16
4	PPh₂Vi	1∶1	Toluene	100	32
5	PPhCy₂	1∶1	Toluene	100	60
6	PPh₂Cy	1∶1	Toluene	100	53
7	PCy₃	1∶1	Toluene	100	42
8	P(ⁿBu)₃	1∶1	Toluene	100	56
9	P(ⁿBu)₃	2.5∶1	Toluene	100	97
10^b	P(ⁿBu)₃	2.5∶1	Toluene	80	99 (96)
11	P(ⁿBu)₃	2.5∶1	Toluene	60	76
12	P(ⁿBu)₃	2.5∶1	Toluene	40	23
13	P(ⁿBu)₃	2.5∶1	Toluene	25	9
14^c	P(ⁿBu)₃	2.5∶1	Toluene	80	72
15	P(ⁿBu)₃	2.5∶1	MeCN	80	12
16	P(ⁿBu)₃	2.5∶1	DCE	80	44
17	P(ⁿBu)₃	2.5∶1	DCM	80	57
18	P(ⁿBu)₃	2.5∶1	MTBE	80	trace
19	L1	2.5∶1	Toluene	80	ND
20	L2	2.5∶1	Toluene	80	ND
21	L3	2.5∶1	Toluene	80	ND
22	L4	2.5∶1	Toluene	80	ND
23	L5	2.5∶1	Toluene	80	ND
24	L6	2.5∶1	Toluene	80	ND
25^d	L7	2.5∶1	Toluene	80	7

Entry	Ligand	1a/2a	Solvent	T/℃	Yield/%
1	DPPM	1∶1	Toluene	100	<5
2	P(p-MeC₆H₄)₃	1∶1	Toluene	100	32
3	P(ⁿBu)Ad₂	1∶1	Toluene	100	16
4	PPh₂Vi	1∶1	Toluene	100	32
5	PPhCy₂	1∶1	Toluene	100	60
6	PPh₂Cy	1∶1	Toluene	100	53
7	PCy₃	1∶1	Toluene	100	42
8	P(ⁿBu)₃	1∶1	Toluene	100	56
9	P(ⁿBu)₃	2.5∶1	Toluene	100	97
10^b	P(ⁿBu)₃	2.5∶1	Toluene	80	99 (96)
11	P(ⁿBu)₃	2.5∶1	Toluene	60	76
12	P(ⁿBu)₃	2.5∶1	Toluene	40	23
13	P(ⁿBu)₃	2.5∶1	Toluene	25	9
14^c	P(ⁿBu)₃	2.5∶1	Toluene	80	72
15	P(ⁿBu)₃	2.5∶1	MeCN	80	12
16	P(ⁿBu)₃	2.5∶1	DCE	80	44
17	P(ⁿBu)₃	2.5∶1	DCM	80	57
18	P(ⁿBu)₃	2.5∶1	MTBE	80	trace
19	L1	2.5∶1	Toluene	80	ND
20	L2	2.5∶1	Toluene	80	ND
21	L3	2.5∶1	Toluene	80	ND
22	L4	2.5∶1	Toluene	80	ND
23	L5	2.5∶1	Toluene	80	ND
24	L6	2.5∶1	Toluene	80	ND
25^d	L7	2.5∶1	Toluene	80	7

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镍催化苯并硅杂环丁烷与酰基硅烷的[4＋2]环化反应

Nickel-Catalyzed [4＋2] Cyclization of Benzosilacyclobutenes and Acylsilanes

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