Chemoselective electrocatalytic hydroboration of alkynes with pinacolborane

Qiu, Hui; Lv, Kang; Qu, Haoqi; Zhang, Xuguang; Yuan, Taoyue; Yao, Weiwei; Xue, Fei; Ma, Mengtao

doi:10.1016/j.molstruc.2022.133463

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Hydroboration Of Unsaturated Compounds1

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2023

2024

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Cited by 6 publications

(2 citation statements)

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“…In the following year, Ma and co-workers reported the electrochemical hydroboration of alkynes with HBpin to afford alkenyl boronate esters (Scheme 10b). 27 In a similar manner, the same group also achieved the electrochemical hydroboration of aldehydes and ketones with HBpin (Scheme 10c). 28…”

Section: Hydroboration Of Unsaturated Compoundsmentioning

confidence: 97%

Electrochemical synthesis and transformation of organoboron compounds

et al. 2023

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Section: Hydroboration Of Unsaturated Compoundsmentioning

confidence: 97%

Electrochemical synthesis and transformation of organoboron compounds

et al. 2023

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“…[25] The authors suggested an oxidation of HBPin with the Hünig base, as an electromediator, followed by a proton loss. HBPin was also employed by Ma and Yao in two other electrochemical methods for the radical hydroboration of alkynes, [26] and carbonyls. [27] In these works, they suggested a direct oxidation of HBPin with proton loss at the carbon anode.…”

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Photocatalytic and Electrochemical Borylation and Silylation Reactions

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Jubault

et al. 2023

The Chemical Record

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Due to their high versatility borylated and silylated compounds are inevitable synthons for organic chemists. To escape the classical hydroboration/hydrosilylation paradigm, chemists turned their attention to more modern and green methods such as photoredox chemistry and electrosynthesis. This account focuses on novel methods for the generation of boryl and silyl radicals to forge C−B and C−Si bonds from our group.

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Metal‐Free Electrochemical Hydroboration of Olefins

et al. 2023

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Herein, we reported the electrochemical hydroboration of olefins to access the organoboron derivatives in a one-pot reaction under air and at room temperature. This reaction manifold was applied to a broad range of alkenes with 40-90% yields and good functional group tolerance without using a metal catalyst or an additional hydride source. Mechanistic studies suggested that this anodic oxidation conducted in an undivided cell allowing the production of a boron radical species, which initiates the hydroboration of olefins event by a radical addition process.

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Chemoselective electrocatalytic hydroboration of alkynes with pinacolborane

Cited by 6 publications

References 39 publications

Electrochemical synthesis and transformation of organoboron compounds

Electrochemical synthesis and transformation of organoboron compounds

Photocatalytic and Electrochemical Borylation and Silylation Reactions

Metal‐Free Electrochemical Hydroboration of Olefins

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