A bottleable super-electron-donor for catalytic borylation of aryl halides

Xu, Youqian; Ming, Wenbo; Xiang, Libo; Ye, Qing

doi:10.1039/d3cc01435e

Chem. Commun.

2023

DOI: 10.1039/d3cc01435e

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A bottleable super-electron-donor for catalytic borylation of aryl halides

Youqian Xu

Wenbo Ming

Libo Xiang

et al.

Abstract: [(Dpp-bian)B(DMAP)]2 (dpp-bian = 1,2-bis[(2,6-diisopropylphenyl)imino]acenaphthene, DMAP = 4-(dimethylamino)pyridine), a bottleable super electron donor (SED), was demonstrated to serve as a SED catalyst in the borylation of aryl iodides, bromides, and the...

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Cited by 3 publications

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Single-Electron Reduction of “Push–Pull” C–C Single Bond and Decyanation Using Tertiary Amines as the Organic Electron Donor

Li,

Sun,

Zhang

et al. 2024

J. Org. Chem.

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Using commercially available tertiary amines as an organic electron donor (OED), the reduction of "push−pull" C−C single bond and reductive decyanation of tetrahydroisoquinolines were realized. These reactions exhibited higher reaction efficiency and better functional group tolerance compared with those of metallic reductants, and the mechanistic study indicated that a radical intermediate was involved in the reduction of the C−C single bond, which provides a new way to the OED-enabled mild reduction.

show abstract

Single-Electron Reduction of “Push–Pull” C–C Single Bond and Decyanation Using Tertiary Amines as the Organic Electron Donor

Li,

Sun,

Zhang

et al. 2024

J. Org. Chem.

View full text Add to dashboard Cite

show abstract

Organic Bases as the Organic Electron Donors (OED) Promoted Reductive Coupling of Diarylhalomethanes: Halogens Controlled Construction of Tetraarylethylenes and Tetraarylethanes

Li,

Mao,

Zhang

et al. 2024

J. Org. Chem.

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Using the organic base as the organic electron donors, the reductive coupling of diaryhalomethanes was smoothly achieved under transition-metal-free reaction conditions, giving a series of synthetically important tetraarylethylenes and tetraarylethanes in high yields. The mechanistic study revealed that the organic bases acting as the electron donor initiated the generation of a radical intermediate, realizing the construction of tetraarylethylene and tetraarylethane skeletons.

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Antiaromatic 2-Azaboroles with π⁴σ² Electronic Configuration

Tan,

Chen,

Liu

et al. 2024

J. Am. Chem. Soc.

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A bottleable super-electron-donor for catalytic borylation of aryl halides

Abstract: [(Dpp-bian)B(DMAP)]2 (dpp-bian = 1,2-bis[(2,6-diisopropylphenyl)imino]acenaphthene, DMAP = 4-(dimethylamino)pyridine), a bottleable super electron donor (SED), was demonstrated to serve as a SED catalyst in the borylation of aryl iodides, bromides, and the...

Cited by 3 publications

References 45 publications

Single-Electron Reduction of “Push–Pull” C–C Single Bond and Decyanation Using Tertiary Amines as the Organic Electron Donor

Single-Electron Reduction of “Push–Pull” C–C Single Bond and Decyanation Using Tertiary Amines as the Organic Electron Donor

Organic Bases as the Organic Electron Donors (OED) Promoted Reductive Coupling of Diarylhalomethanes: Halogens Controlled Construction of Tetraarylethylenes and Tetraarylethanes

Antiaromatic 2-Azaboroles with π⁴σ² Electronic Configuration

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A bottleable super-electron-donor for catalytic borylation of aryl halides

Abstract: [(Dpp-bian)B(DMAP)]2 (dpp-bian = 1,2-bis[(2,6-diisopropylphenyl)imino]acenaphthene, DMAP = 4-(dimethylamino)pyridine), a bottleable super electron donor (SED), was demonstrated to serve as a SED catalyst in the borylation of aryl iodides, bromides, and the...

Cited by 3 publications

References 45 publications

Single-Electron Reduction of “Push–Pull” C–C Single Bond and Decyanation Using Tertiary Amines as the Organic Electron Donor

Single-Electron Reduction of “Push–Pull” C–C Single Bond and Decyanation Using Tertiary Amines as the Organic Electron Donor

Organic Bases as the Organic Electron Donors (OED) Promoted Reductive Coupling of Diarylhalomethanes: Halogens Controlled Construction of Tetraarylethylenes and Tetraarylethanes

Antiaromatic 2-Azaboroles with π4σ2 Electronic Configuration

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Product

Resources

About

Antiaromatic 2-Azaboroles with π⁴σ² Electronic Configuration