4.8 Article

Diphenylsilylsilanolates Enable the Transfer of a Wide Range of Silyl Groups

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ORGANIC LETTERS
Volume -, Issue -, Pages -

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c03558

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Funding

  1. JSPS KAKENHI, Japan [JP21H01934, JP20J23393, JP19H00895]
  2. JST CREST, Japan [JPMJCR19R4]
  3. JSPS Predoctoral Fellowship
  4. Sumitomo Foundation

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In this study, we introduce sodium diphenylsilylsilanolates as new stable and convenient silylating reagents, which can be synthesized from chlorosilanes. The new reagents exhibit the ability to deliver various silyl groups in palladium-catalyzed silylation of aryl bromides, regardless of the steric and electronic properties of the silyl groups to be transferred.
Development of silylating reagents that can transfer a wide range of silyl groups has been a long-standing challenge. Herein we report sodium diphenylsilylsilanolates as new stable and handy silylating reagents that could be synthesized from chlorosilanes. The new reagents retain the ability of dimethylsilylsilanolates for the delivery of a variety of silyl groups in palladium-catalyzed silylation of aryl bromides irrespective of the steric and electronic properties of silyl groups to be transferred.

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