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α-Borylalkyl radicals: their distinctive reactivity in modern organic synthesis

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Abstract

Organoborons are extremely important for synthetic organic chemistry; they can serve as advanced intermediates for a variety of transformations. Such a well-known transformation involves the loss of the boron moiety, creating alkyl radicals. Although these originally developed protocols for alkyl radical generation remain in active use today, in recent years their α-boryl carbon-centred radicals have been joined by a new array of radical generation strategies that offer a unique reactivity to forge a wider diversity of organoborons that often operate under mild and benign conditions. Herein, we will highlight the stability and reactivity of α-borylalkyl radicals and their remarkably recent advances in order to further utilise them for C–C and C–heteroatom bond formation. Their use for this purpose has been reported over the last decade in an attempt to guide the synthetic community. Various transition-metal and metal-free methods for their generation are presented, and more advanced photoredox approaches are discussed, mainly for the period of 2009–2019.

Graphical abstract: α-Borylalkyl radicals: their distinctive reactivity in modern organic synthesis

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Publication details

The article was received on 13 Oct 2019, accepted on 27 Nov 2019 and first published on 27 Nov 2019


Article type: Highlight
DOI: 10.1039/C9CC08027A
Chem. Commun., 2020, Advance Article

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    α-Borylalkyl radicals: their distinctive reactivity in modern organic synthesis

    N. Kumar, R. R. Reddy, N. Eghbarieh and A. Masarwa, Chem. Commun., 2020, Advance Article , DOI: 10.1039/C9CC08027A

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