Metal-Free Addition of Boronic Acids to Silylnitronates

Mansour Dolé Kerim; Pakoupati Boyode; Julian Garrec; Laurent El Kaïm

doi:10.1055/s-0039-1690845

Metal-Free Addition of Boronic Acids to Silylnitronates

Mansour Dolé Kerim
, Pakoupati Boyode
, Julian Garrec
, Laurent El Kaïm

Centre national de la recherche scientifique
Université de Lomé

Research output: Contribution to journal › Article › peer-review

Abstract

We report for the first time a metal-free addition of boronic acids to silylnitronates to afford oxime derivatives through aryl transfer on the carbon nitrogen double bond. A reaction mechanism has been proposed in relation with a DFT study on the key aryl transfer. This arylation process is effective for cycloalkenyl nitro derivatives leading to oximes that may be oxidatively converted into 3-Arylisoxazole derivatives.

Original language	English
Pages (from-to)	856-860
Number of pages	5
Journal	Synlett
Volume	31
Issue number	9
DOIs	https://doi.org/10.1055/s-0039-1690845
Publication status	Published - 14 May 2020

Keywords

boronic acid
isoxazole
nitro
oxime
silyl nitronate

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10.1055/s-0039-1690845

Cite this

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title = "Metal-Free Addition of Boronic Acids to Silylnitronates",

abstract = "We report for the first time a metal-free addition of boronic acids to silylnitronates to afford oxime derivatives through aryl transfer on the carbon nitrogen double bond. A reaction mechanism has been proposed in relation with a DFT study on the key aryl transfer. This arylation process is effective for cycloalkenyl nitro derivatives leading to oximes that may be oxidatively converted into 3-Arylisoxazole derivatives.",

keywords = "boronic acid, isoxazole, nitro, oxime, silyl nitronate",

author = "Kerim, \{Mansour Dol{\'e}\} and Pakoupati Boyode and Julian Garrec and \{El Ka{\"i}m\}, Laurent",

year = "2020",

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language = "English",

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pages = "856--860",

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T1 - Metal-Free Addition of Boronic Acids to Silylnitronates

AU - Kerim, Mansour Dolé

AU - Boyode, Pakoupati

AU - Garrec, Julian

AU - El Kaïm, Laurent

PY - 2020/5/14

Y1 - 2020/5/14

N2 - We report for the first time a metal-free addition of boronic acids to silylnitronates to afford oxime derivatives through aryl transfer on the carbon nitrogen double bond. A reaction mechanism has been proposed in relation with a DFT study on the key aryl transfer. This arylation process is effective for cycloalkenyl nitro derivatives leading to oximes that may be oxidatively converted into 3-Arylisoxazole derivatives.

AB - We report for the first time a metal-free addition of boronic acids to silylnitronates to afford oxime derivatives through aryl transfer on the carbon nitrogen double bond. A reaction mechanism has been proposed in relation with a DFT study on the key aryl transfer. This arylation process is effective for cycloalkenyl nitro derivatives leading to oximes that may be oxidatively converted into 3-Arylisoxazole derivatives.

KW - boronic acid

KW - isoxazole

KW - nitro

KW - oxime

KW - silyl nitronate

U2 - 10.1055/s-0039-1690845

DO - 10.1055/s-0039-1690845

M3 - Article

AN - SCOPUS:85088267836

SN - 0936-5214

VL - 31

SP - 856

EP - 860

JO - Synlett

JF - Synlett

IS - 9

ER -

Metal-Free Addition of Boronic Acids to Silylnitronates

Abstract

Keywords

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