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通过苯并唑和硅烷的氢硅烷化和重排级联反应直接合成硅苯并唑。

Direct synthesis of sila-benzoazoles through hydrosilylation and rearrangement cascade reaction of benzoazoles and silanes.

机构信息

State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University Changchun, Jilin, 130012, China.

Key Laboratory of Mesoscopic Chemistry of Ministry of Education, Institute of Theoretical and Computational Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, China.

出版信息

Nat Commun. 2023 Feb 9;14(1):703. doi: 10.1038/s41467-023-36360-z.

Abstract

Sila-isosteres have attracted increasing attention due to their potential application in a variety of fields and their different properties compared to their carbon-containing analogs. However, the preparation of these silicon-containing compound remains challenging and thus the development of alternative synthetic methodologies is desirable. Here, we employ B(CF) as catalyst to enable the synthesis of highly functionalized sila-benzoazoles via hydrosilylation and rearrangement cascade reaction of benzoazoles and commercially available silanes. This strategy also exhibits remarkable features such as 100% atom-economy, good functional group tolerance, broad substrate scope, easy scale-up and good catalytic performance, demonstrating its potential application in sila-isostere synthesis.

摘要

硅同系物由于其在多种领域的潜在应用以及与含碳同系物相比的不同性质而受到越来越多的关注。然而,这些含硅化合物的制备仍然具有挑战性,因此需要开发替代的合成方法。在这里,我们采用 B(CF)作为催化剂,通过苯并唑和市售硅烷的氢硅化和重排级联反应,实现了高度官能化的硅苯并氮唑的合成。该策略还具有 100%原子经济性、良好的官能团耐受性、广泛的底物范围、易于规模化和良好的催化性能等显著特点,展示了其在硅同系物合成中的潜在应用。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/eac6/9911738/8d3be1f27d6c/41467_2023_36360_Fig1_HTML.jpg

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