TY - JOUR
T1 - α-Borylalkyl radicals
T2 - Their distinctive reactivity in modern organic synthesis
AU - Kumar, Nivesh
AU - Reddy, Reddy Rajasekhar
AU - Eghbarieh, Nadim
AU - Masarwa, Ahmad
N1 - Publisher Copyright:
© 2019 The Royal Society of Chemistry.
PY - 2020
Y1 - 2020
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85076693693&partnerID=8YFLogxK
U2 - 10.1039/c9cc08027a
DO - 10.1039/c9cc08027a
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C2 - 31803873
AN - SCOPUS:85076693693
SN - 1359-7345
VL - 56
SP - 13
EP - 25
JO - Chemical Communications
JF - Chemical Communications
IS - 1
ER -