TY - JOUR
T1 - Photoredox-Mediated Deoxygenative Radical Additions of Aromatic Acids to Vinyl Boronic Esters and gem-Diborylalkenes**
AU - Nagaraju, Anugula
AU - Saiaede, Tamer
AU - Eghbarieh, Nadim
AU - Masarwa, Ahmad
N1 - Publisher Copyright:
© 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
PY - 2023/1/12
Y1 - 2023/1/12
N2 - A new method to access β-keto-gem-diborylalkanes, by direct deoxygenative radical addition of aromatic carboxylic acids to gem-dibortlalkenes, is described. The reaction proceeds under mild photoredox catalysis and involves the photochemical C−O bond activation of aromatic carboxylic acids in the presence of PPh3. It generates an acyl radical, which further undergoes an additional reaction with gem-diborylalkenes to form an α-gem-diboryl alkyl radical intermediate, which then reduces to the corresponding anion, which after protonation, affords the β-keto-gem-diborylalkane product. Moreover, the same scenario has been extended to the vinyl boronic esters, for example, gem-(Ar, Bpin)-alkenes, and gem-(Alkyl, Bpin)-alkenes. Importantly, this protocol provides a general platform for the late-stage functionalization of bio-active and drug molecules containing a carboxylic acid group.
AB - A new method to access β-keto-gem-diborylalkanes, by direct deoxygenative radical addition of aromatic carboxylic acids to gem-dibortlalkenes, is described. The reaction proceeds under mild photoredox catalysis and involves the photochemical C−O bond activation of aromatic carboxylic acids in the presence of PPh3. It generates an acyl radical, which further undergoes an additional reaction with gem-diborylalkenes to form an α-gem-diboryl alkyl radical intermediate, which then reduces to the corresponding anion, which after protonation, affords the β-keto-gem-diborylalkane product. Moreover, the same scenario has been extended to the vinyl boronic esters, for example, gem-(Ar, Bpin)-alkenes, and gem-(Alkyl, Bpin)-alkenes. Importantly, this protocol provides a general platform for the late-stage functionalization of bio-active and drug molecules containing a carboxylic acid group.
KW - carboxylic-acids
KW - deoxygenation
KW - gem-diborylalkenes
KW - organoborones
KW - photochemistry
UR - http://www.scopus.com/inward/record.url?scp=85143210803&partnerID=8YFLogxK
U2 - 10.1002/chem.202202646
DO - 10.1002/chem.202202646
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C2 - 36222076
AN - SCOPUS:85143210803
SN - 0947-6539
VL - 29
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 3
M1 - e202202646
ER -