Synthesis of Organoboronic Acids, Organoboronates, and Related Compounds

doi:10.1002/9781119015789.ch6

Practical Functional Group Synthesis 2016

DOI: 10.1002/9781119015789.ch6

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Synthesis of Organoboronic Acids, Organoboronates, and Related Compounds

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Cited by 3 publications

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Air‐Stable Organoradical Boron Reagents

Wang

Liu

et al. 2023

Angewandte Chemie

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Both organic radicals and organoboron reagents have been broadly investigated, but the combination of them via direct C−H borylation as organic radical building blocks has never been achieved. Herein, a series of organoradical boron reagents, such as TTM‐Bpin and TTM‐BOH, were synthesized through the key step of C−H borylation of substrate TTM‐H ((2,6‐dichlorophenyl) bis(2,4,6‐trichlorophenyl)methyl) radical for the first time. They are air stable enough to be stored in the solid state for several months under dark conditions, and fully investigated through single crystal analysis, EPR and DFT calculations. Furthermore, they can smoothly work in the standard Suzuki–Miyaura coupling (SMC) reaction with retention of the carbon radical center. Meanwhile, these radical species bearing different boron units display fluorescent character and are potentially applied for the collective synthesis of luminescent organic radicals, as well as other functionalized open‐shell materials.

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Air‐Stable Organoradical Boron Reagents

Wang

Liu

et al. 2023

Angewandte Chemie

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Air‐Stable Organoradical Boron Reagents

Wang

Liu

et al. 2023

Angew Chem Int Ed

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Both organic radicals and organoboron reagents have been broadly investigated, but the combination of them via direct CÀ H borylation as organic radical building blocks has never been achieved. Herein, a series of organoradical boron reagents, such as TTM-Bpin and TTM-BOH, were synthesized through the key step of CÀ H borylation of substrate TTM-H ((2,6dichlorophenyl) bis(2,4,6-trichlorophenyl)methyl) radical for the first time. They are air stable enough to be stored in the solid state for several months under dark conditions, and fully investigated through single crystal analysis, EPR and DFT calculations. Furthermore, they can smoothly work in the standard Suzuki-Miyaura coupling (SMC) reaction with retention of the carbon radical center. Meanwhile, these radical species bearing different boron units display fluorescent character and are potentially applied for the collective synthesis of luminescent organic radicals, as well as other functionalized open-shell materials.

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Vanadium-Catalyzed Stereo- and Regioselective Hydroboration of Alkynes to Vinyl Boronates

et al. 2022

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Molecular complexes of vanadium catalyze cis-selective anti-Markovnikov hydroboration of alkynes to generate vinyl boronate esters with appreciable turnover numbers of up to 4000 at room temperature. This represents the first example of the use of vanadium in homogeneous catalytic hydroboration of alkynes. The method is tolerant to various functional groups, including CC double bonds. Accordingly, 1-hexen-5-yne can be quantitatively and selectively reduced at the triple bond, leaving the double bond unaffected. Preliminary computational analysis of the catalytic cycle reveals both two-state reactivity and previously unknown complexity associated with the redox-active ligand. Specifically, it was found that the ligand can shuttle up to two electrons back-and-forth to and from the metal, which thus adapts three different oxidation states on the catalytic reaction coordinate.

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Synthesis of Organoboronic Acids, Organoboronates, and Related Compounds

Cited by 3 publications

References 108 publications

Air‐Stable Organoradical Boron Reagents

Air‐Stable Organoradical Boron Reagents

Air‐Stable Organoradical Boron Reagents

Vanadium-Catalyzed Stereo- and Regioselective Hydroboration of Alkynes to Vinyl Boronates

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