Synlett 2024; 35(11): 1296-1300
DOI: 10.1055/a-2191-5906
cluster
Japan/Netherlands Gratama Workshop

Efficient Protosilylation of Unsaturated Compounds with Silylboronates over a Heterogeneous Cu3N Nanocube Catalyst

Hang Xu
a   Department of Materials Engineering Science, Graduate School of Engineering Science, Osaka University, 1–3 Machikaneyama, Toyonaka, Osaka 560–8531, Japan
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a   Department of Materials Engineering Science, Graduate School of Engineering Science, Osaka University, 1–3 Machikaneyama, Toyonaka, Osaka 560–8531, Japan
b   Innovative Catalysis Science Division, Institute for Open and Transdisciplinary Research Initiatives (ICS-OTRI), Osaka University, Suita, Osaka 565–0871, Japan
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a   Department of Materials Engineering Science, Graduate School of Engineering Science, Osaka University, 1–3 Machikaneyama, Toyonaka, Osaka 560–8531, Japan
b   Innovative Catalysis Science Division, Institute for Open and Transdisciplinary Research Initiatives (ICS-OTRI), Osaka University, Suita, Osaka 565–0871, Japan
c   PRESTO, Japan Science and Technology Agency (JST), 4–1–8 Honcho, Kawaguchi, Saitama 333–0012, Japan
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a   Department of Materials Engineering Science, Graduate School of Engineering Science, Osaka University, 1–3 Machikaneyama, Toyonaka, Osaka 560–8531, Japan
b   Innovative Catalysis Science Division, Institute for Open and Transdisciplinary Research Initiatives (ICS-OTRI), Osaka University, Suita, Osaka 565–0871, Japan
d   Research Center for Solar Energy Chemistry, Graduate School of Engineering Science, Osaka University, 1–3 Machikaneyama, Toyonaka, Osaka 560–8531, Japan
› Author Affiliations
This study was supported by JSPS KAKENHI (grants nos. 20H02523 and 21K04776) and JST PRESTO (grant no. JPMJPR21Q9). This study was partially supported by the JST-CREST (grant no. JPMJCR21L5). Part of the experimental analysis was supported by the ‘Advanced Research Infrastructure for Materials and Nanotechnology in Japan (ARIM)’ (grant no. JPMXP1222HK0062) of the Ministry of Education, Culture, Sports, Science, and Technology (MEXT).


Abstract

Copper-catalyzed protosilylation of unsaturated compounds with silylboronates has attracted attention for the production of organosilanes; however, the use of organic ligands or bases is unavoidable. Herein, we report a heterogeneous catalytic system for the protosilylation of unsaturated compounds with silylboronates under mild and additive-free conditions over copper nitride nanocubes (Cu3N NCs). This method can be applied to various substrates (e.g., alkynes, alkenes, or imines) to afford the corresponding organosilicon compounds. The Cu3N NC catalyst can be easily recovered and reused several times. Thus, the active and reusable Cu3N NC catalyst offers a green and sustainable method for efficient organosilane production.

Supporting Information



Publication History

Received: 20 September 2023

Accepted after revision: 13 October 2023

Accepted Manuscript online:
13 October 2023

Article published online:
17 November 2023

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