Metal-free tandem cyclization/hydrosilylation to construct tetrahydroquinoxalines

A one-pot tandem procedure involving cyclization and sequential hydrosilylation of imines and amides under the catalysis of B(C 6 F 5 ) 3 has been developed for the step-economical construction of 1,2,3,4-tetrahydroquinoxalines directly from readily available 1,2-diaminobenzenes, α-ketoesters and lo...

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Published inGreen chemistry : an international journal and green chemistry resource : GC Vol. 20; no. 2; pp. 403 - 411
Main Authors Pan, Yixiao, Chen, Changjun, Xu, Xin, Zhao, Haoqiang, Han, Jiahong, Li, Huanrong, Xu, Lijin, Fan, Qinghua, Xiao, Jianliang
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 2018
Royal Society of Chemistry
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ISSN1463-9262
1463-9270
1463-9270
DOI10.1039/C7GC03095A

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Summary:A one-pot tandem procedure involving cyclization and sequential hydrosilylation of imines and amides under the catalysis of B(C 6 F 5 ) 3 has been developed for the step-economical construction of 1,2,3,4-tetrahydroquinoxalines directly from readily available 1,2-diaminobenzenes, α-ketoesters and low-cost, safe polymethylhydrosiloxane (PMHS). This metal-free approach provides various products in good to excellent yields, and displays a wide range of substrate scope and a high degree of functional group tolerance even to reduction-sensitive moieties. The choice of hydrosilanes is critical to the catalysis, and PMHS has proved to be optimal. Decreasing the amount of PMHS could enable the reaction to stop at the 3,4-dihydroquinoxalin-2(1 H )-one stage. The procedure is convenient and scalable, and neither a dried solvent nor an inert atmosphere is required. Moreover, the enantioselective construction of these products was explored, and promising results were achieved.
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ISSN:1463-9262
1463-9270
1463-9270
DOI:10.1039/C7GC03095A