Synthesis of the Hydrosilicon Species via Oxidative Addition of Silylene toward the Proton-Containing Molecules

doi:10.6023/cjoc202309007

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (4): 1311-1318.DOI: 10.6023/cjoc202309007 Previous Articles Next Articles

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硅宾与质子氢分子的氧化加成反应合成硅氢物种

孔德亮, 杨萧昂, 赵怡玲, 彭彦博, 朱红平^*()

厦门大学化学化工学院固体表面物理化学国家重点实验室厦门 361005

收稿日期:2023-09-07 修回日期:2023-10-24 发布日期:2023-11-23
作者简介:† 共同第一作者.
基金资助:
国家自然科学基金(21972112); 福建省产学研(2021H6002)

Synthesis of the Hydrosilicon Species via Oxidative Addition of Silylene toward the Proton-Containing Molecules

Deliang Kong, Xiaoang Yang, Yiling Zhao, Yanbo Peng, Hongping Zhu()

State Key Laboratory of Physical Chemistry of Solid Surfaces, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005

Received:2023-09-07 Revised:2023-10-24 Published:2023-11-23
Contact: * E-mail: hpzhu@xmu.edu.cn
About author:† The authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(21972112); Productive Research Program of Fujian Province(2021H6002)

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Abstract

The oxidative addition reaction of silylenes with proton-containing molecules is an effective method for synthesis of hydrosilicon species. Herein, amidinatoborylaminosilylenes (L)[(1,5-C₈H₁₄)B(R)N]Si [L=PhC(N^tBu)₂; R=2,4,6-Me₃C₆H₂ (1), 2,6-ⁱPr₂C₆H₃ (2), 1-C₁₀H₁₅ (3)] were employed, each of which reacted with 1-(diphenylmethyl)-3-hydroxyazetidine to produce the derived alkoxyl hydrosilicon compounds (L)[(1,5-C₈H₁₄)B(R)N]Si(H)[O-cyclo-CH(CH₂)₂N(CHPh₂)] (4~6), and with mercaptans as 2-naphthalenethiol, 4-fluorothiophenol, 2-chlorobenzenethiol to yield thiol hydrosilicon compounds (L)- [(1,5-C₈H₁₄)B(R)N]Si(H)(SR') (7~14). Silylene 1 reacted with diphenylamine to give (L)[(1,5-C₈H₁₄)B(2,4,6-Me₃C₆H₂)N]- Si(H)(NPh₂) (15). Compounds 4~15 have been characterized by NMR spectra and elemental analysis, of which 5, 7 and 11 were further confirmed by X-ray crystallography. Compounds 4~15 are the hydrosilicon species with novel structures and compositions, all of which are bonded by four different groups, being generated by the oxidative addition reaction via the silylene Si: center toward the respective O—H, S—H, and N—H bonds of the proton-containing molecules, where a mode of a charge reversal of the proton into the hydride group at the Si center is realized.

Key words: silylene, proton-containing molecule, oxidative addition reaction, hydrosilicon compound

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Deliang Kong, Xiaoang Yang, Yiling Zhao, Yanbo Peng, Hongping Zhu. Synthesis of the Hydrosilicon Species via Oxidative Addition of Silylene toward the Proton-Containing Molecules[J]. Chinese Journal of Organic Chemistry, 2024, 44(4): 1311-1318.

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Fig. & Tab. 6

Scheme 1. Synthesis of compounds 4~6

Scheme 2. Synthesis of compounds 7~14

Scheme 3. Synthesis of compound 15

Figure 1. X-ray crystal structure of 5 and the important bond lengths (nm) H atoms except for that of the SiH are omitted for clarity. Selected bond lengths (nm): Si(1)—O(1) 0.1647(2), Si(1)—N(2) 0.1731(2), Si(1)—N(3) 0.2734(2), Si(1)—N(4) 0.1753(2), Si(1)—H(1) 0.1460(20).

Figure 2. X-ray crystal structure of 7 and the important bond lengths (nm) H atoms except for that of the Si—H are omitted for clarity. Selected bond lengths (nm): Si(1)—S(1) 0.2182(7), Si(1)—N(1) 0.1786(2), Si(1)—N(2) 0.2127(2), Si(1)—N(3) 0.1818(2), Si(1)—H(1) 0.1417(17).

Figure 3. X-ray crystal structure of 11 and the important bond lengths (nm) H atoms except for that of the SiH are omitted for clarity. Selected bond lengths (nm): Si(1)—S(1) 0.2160(2), Si(1)—N(1) 0.1784(4), Si(1)—N(2) 0.1798(4), Si(1)—N(3) 0.2253(4), Si(1)—H(1) 0.1430(40).

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硅宾与质子氢分子的氧化加成反应合成硅氢物种

Synthesis of the Hydrosilicon Species via Oxidative Addition of Silylene toward the Proton-Containing Molecules

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