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Synlett 2023; 34(04): 369-373
DOI: 10.1055/a-1982-5185
letter

Palladium-Catalyzed C(sp2)–H Silylation via a Native-Amine-Directed Strategy

Yintao Yan‡
a   School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Nanjing, Jiangsu 210094, P. R. of China
,
Xuan Wang‡
a   School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Nanjing, Jiangsu 210094, P. R. of China
,
Jianhua Li∗
b   Lianhe Chemical Technology Co., Ltd., Jiangkou Avenue, Taizhou, Zhejiang 318020, P. R. of China
,
Chao Jiang  ∗
a   School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Nanjing, Jiangsu 210094, P. R. of China
› Author AffiliationsThis work was supported by the National Natural Science Foundation of China (NSFC, Grant No. 21772092).
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Abstract

A palladium-catalyzed C(sp2)–H silylation of morpholinones to afford silyl morpholinones is reported. The native secondary amine, which is tolerated in the reaction, is able to promote the C–H activation and silylation of the aryl group. The substrates are monosilylated selectively and tolerate various functional groups. The resulting silyl morpholinone derivatives are potentially useful in pharmaceuticals and agrochemicals.

Key words

palladium - C–H activation - C(sp2)–H Silylation - morpholinone - organosilicon compounds

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1982-5185.
  • Supporting Information


Publication History

Received: 19 October 2022

Accepted after revision: 18 November 2022

Accepted Manuscript online:
18 November 2022

Article published online:
19 December 2022

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