Hydroalkylation of styrenes enabled by boryl radical mediated halogen atom transfer

Serena Pillitteri; Rajat Walia; Erik V. Van der Eycken; Upendra K. Sharma

doi:10.1039/d4sc01731e

Hydroalkylation of styrenes enabled by boryl radical mediated halogen atom transfer

Serena Pillitteri, Rajat Walia, Erik V. Van der Eycken, Upendra K. Sharma^*

^*Corresponding author for this work

Department of Chemistry

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

13 Citations (Scopus)

34 Downloads (CityUHK Scholars)

Abstract

In this study, we present an inexpensive, stable, and easily available boryl radical source (BPh₄Na) employed in a Halogen Atom Transfer (XAT) methodology. This mild and convenient strategy unlocks the use of not only alkyl iodides as radical precursors but also of the more challenging alkyl and aryl bromides to generate C-centered radicals. The generated radicals were further engaged in the anti-Markovnikov hydroalkylation of electronically diverse styrenes, therefore achieving the formation of C(sp³)-C(sp³) and C(sp³)-C(sp²) bonds. A series of experimental and computational studies revealed the prominent role of BPh₄Na in the halogen abstraction step. © 2024 The Author(s).

Original language	English
Pages (from-to)	8813-8819
Number of pages	7
Journal	Chemical Science
Volume	15
Issue number	23
Online published	3 May 2024
DOIs	https://doi.org/10.1039/d4sc01731e
Publication status	Published - 21 Jun 2024

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This full text is made available under CC-BY-NC 3.0. https://creativecommons.org/licenses/by-nc/3.0/

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title = "Hydroalkylation of styrenes enabled by boryl radical mediated halogen atom transfer",

abstract = "In this study, we present an inexpensive, stable, and easily available boryl radical source (BPh4Na) employed in a Halogen Atom Transfer (XAT) methodology. This mild and convenient strategy unlocks the use of not only alkyl iodides as radical precursors but also of the more challenging alkyl and aryl bromides to generate C-centered radicals. The generated radicals were further engaged in the anti-Markovnikov hydroalkylation of electronically diverse styrenes, therefore achieving the formation of C(sp3)-C(sp3) and C(sp3)-C(sp2) bonds. A series of experimental and computational studies revealed the prominent role of BPh4Na in the halogen abstraction step. {\textcopyright} 2024 The Author(s).",

author = "Serena Pillitteri and Rajat Walia and {Van der Eycken}, {Erik V.} and Sharma, {Upendra K.}",

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T1 - Hydroalkylation of styrenes enabled by boryl radical mediated halogen atom transfer

AU - Pillitteri, Serena

AU - Walia, Rajat

AU - Van der Eycken, Erik V.

AU - Sharma, Upendra K.

PY - 2024/6/21

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N2 - In this study, we present an inexpensive, stable, and easily available boryl radical source (BPh4Na) employed in a Halogen Atom Transfer (XAT) methodology. This mild and convenient strategy unlocks the use of not only alkyl iodides as radical precursors but also of the more challenging alkyl and aryl bromides to generate C-centered radicals. The generated radicals were further engaged in the anti-Markovnikov hydroalkylation of electronically diverse styrenes, therefore achieving the formation of C(sp3)-C(sp3) and C(sp3)-C(sp2) bonds. A series of experimental and computational studies revealed the prominent role of BPh4Na in the halogen abstraction step. © 2024 The Author(s).

AB - In this study, we present an inexpensive, stable, and easily available boryl radical source (BPh4Na) employed in a Halogen Atom Transfer (XAT) methodology. This mild and convenient strategy unlocks the use of not only alkyl iodides as radical precursors but also of the more challenging alkyl and aryl bromides to generate C-centered radicals. The generated radicals were further engaged in the anti-Markovnikov hydroalkylation of electronically diverse styrenes, therefore achieving the formation of C(sp3)-C(sp3) and C(sp3)-C(sp2) bonds. A series of experimental and computational studies revealed the prominent role of BPh4Na in the halogen abstraction step. © 2024 The Author(s).

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DO - 10.1039/d4sc01731e

M3 - RGC 21 - Publication in refereed journal

C2 - 38873058

SN - 2041-6520

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SP - 8813

EP - 8819

JO - Chemical Science

JF - Chemical Science

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ER -

Hydroalkylation of styrenes enabled by boryl radical mediated halogen atom transfer

Abstract

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