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Synlett 2020; 31(13): 1328-1332
DOI: 10.1055/s-0039-1690877
letter
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Silylation of Aryl Chlorides with Bulky Dialkoxydisilanes

Keitaro Fukui
,
Hayate Saito 
,
Jun Shimokawa  ∗
,
Hideki Yorimitsu  ∗
This work was supported by the Japan Society for the Promotion of Science (JSPS KAKENHI Grant Numbers JP16H04109, JP18H04254, JP18H04409, JP19H00895, JP18J22838), and partly by Core Research for Evolutional Science and Technology (JST CREST Grant Number JPMJCR19R4), Japan. J.S. thanks the support from the Kyoto University Research Development Program (ISHIZUE 2019). H.Y. thanks The Asahi Glass Foundation for financial support.
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Publication History

Received: 02 March 2020

Accepted after revision: 18 March 2020

Publication Date:
02 April 2020 (online)

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Abstract

Arylsilanes bearing a bulky alkoxy group on the silicon were synthesized from aryl chlorides and dialkoxydisilanes under reaction conditions utilizing SingaCycle-A3 as a palladium precatalyst and lithium benzoate in wet DMA. This report proposes the first direct and catalytic method for introducing tert-butoxy- or 1-adamantyloxysilyl groups onto various aryl moieties through the silylation reaction.

Key words

palladium - alkoxysilane - disilane - arylsilane

Supporting Information

 

  • References and Notes

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  • 15 We could not deny the possibility that disilane 5 reacts with Pd(II) benzoate through a concerted six-membered transition state to give silyl benzoate 15 and an Ar–Pd(II)–SiMe2(OtBu) species, which would then generate arylsilane 6 via reductive elimination.