Transition-metal-free, one-pot synthesis of benzoxaboroles from<i>o</i>-bromobenzaldehydes<i>via</i>visible-light-promoted borylation

Luo, Jinghan; Jia, Xingxing; Hu, Yanjun; Chen, Jianchao; Sun, Tiemin

doi:10.1039/d1ob01853a

Org. Biomol. Chem.

2021

DOI: 10.1039/d1ob01853a

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Transition-metal-free, one-pot synthesis of benzoxaboroles fromo-bromobenzaldehydesviavisible-light-promoted borylation

Jinghan Luo

Xingxing Jia

Yanjun Hu

et al.

Abstract: A novel and practical approach for the synthesis of benzoxaboroles from o-bromobenzaldehydes is described via visible-light-promoted borylation.

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Cited by 3 publications

References 33 publications

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Photocatalytic C−I Bond Borylation and Phosphorylation of Diaryliodonium Salts with Excellent Atom‐Economy

Ding,

Guo,

Chen

et al. 2024

Adv Synth Catal

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Highly atom‐economic conversion of diaryliodonium salts represents an underdeveloped but highly desirable domain. Most reactions involving these species only utilize single aryl group of the diaryliodonium and produce an equivalent of aryl iodide as waste. Herein, by further transforming the side‐product aryl iodide, we report an overall new two‐step one‐pot strategy that allows photocatalytic C−I bond borylation and phosphorylation of diaryliodonium salts and ensures effective conversion of both aryl groups of the diaryliodonium into the relevant arylboronic esters or arylphosphonic esters. Mechanistic investigations suggest that electron‐donor‐acceptor (EDA) complex is formed between the photocatalyst phenothiazine (PTH) and diaryliodonium salt substrate. Upon visible light irradiation, this complex produces aryl radical and aryl iodide. With addition of a base in the second step, the reducing ability of the photocatalyst is enhanced via proton‐coupled electron transfer (PCET) process, thereby aryl iodide produced in the first step is reduced to yield aryl radical again. Both aryl radicals generated in the two steps react with B2(OR)4 or P(OR)3 to produce the corresponding monoarylation product in a quantitative yield.

show abstract

Photocatalytic C−I Bond Borylation and Phosphorylation of Diaryliodonium Salts with Excellent Atom‐Economy

Ding,

Guo,

Chen

et al. 2024

Adv Synth Catal

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show abstract

Synthesis, fungicidal activity and molecular docking studies of tavaborole derivatives

Huang

Guo

et al. 2023

Advanced Agrochem

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Selective PARP1 inhibitors, PARP1-based dual-target inhibitors, PROTAC PARP1 degraders, and prodrugs of PARP1 inhibitors for cancer therapy

Peng

Pan

Jiang

et al. 2022

Pharmacological Research

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Transition-metal-free, one-pot synthesis of benzoxaboroles fromo-bromobenzaldehydesviavisible-light-promoted borylation

Abstract: A novel and practical approach for the synthesis of benzoxaboroles from o-bromobenzaldehydes is described via visible-light-promoted borylation.

Cited by 3 publications

References 33 publications

Photocatalytic C−I Bond Borylation and Phosphorylation of Diaryliodonium Salts with Excellent Atom‐Economy

Photocatalytic C−I Bond Borylation and Phosphorylation of Diaryliodonium Salts with Excellent Atom‐Economy

Synthesis, fungicidal activity and molecular docking studies of tavaborole derivatives

Selective PARP1 inhibitors, PARP1-based dual-target inhibitors, PROTAC PARP1 degraders, and prodrugs of PARP1 inhibitors for cancer therapy

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