Visible-Light-Induced Palladium-Catalyzed Cross-Coupling of Iodocarboranes with (Hetero)Arenes

Shimeng Li; Jie Zhang; Zuowei Xie

doi:10.1021/acs.orglett.2c02648

Visible-Light-Induced Palladium-Catalyzed Cross-Coupling of Iodocarboranes with (Hetero)Arenes

Shimeng Li
, Jie Zhang
, Zuowei Xie^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

10 Citations (Scopus)

Abstract

This work describes a general method for the efficient production of a class of cage B-centered carboranyl radicals at the B3, B4, and B9 sites via a visible-light-promoted palladium(0)/palladium(I) pathway using readily available iodo-o-carboranes as the starting materials. The electrophilicities of these hypervalent boron-centered radicals decrease in the following order: B3 > B4 > B9. They are useful intermediates for the preparation of a family of cage B-(hetero)arylated o-carboranes at ambient temperature.

Original language	English
Pages (from-to)	7497-7501
Number of pages	5
Journal	Organic Letters
Volume	24
Issue number	41
Early online date	6 Oct 2022
DOIs	https://doi.org/10.1021/acs.orglett.2c02648
Publication status	Published - 21 Oct 2022

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title = "Visible-Light-Induced Palladium-Catalyzed Cross-Coupling of Iodocarboranes with (Hetero)Arenes",

abstract = "This work describes a general method for the efficient production of a class of cage B-centered carboranyl radicals at the B3, B4, and B9 sites via a visible-light-promoted palladium(0)/palladium(I) pathway using readily available iodo-o-carboranes as the starting materials. The electrophilicities of these hypervalent boron-centered radicals decrease in the following order: B3 > B4 > B9. They are useful intermediates for the preparation of a family of cage B-(hetero)arylated o-carboranes at ambient temperature.",

author = "Shimeng Li and Jie Zhang and Zuowei Xie",

note = "This work was supported by grants from the Hong Kong Research Grants Council (Projects 14305117 and 14305420). Publisher Copyright: {\textcopyright} 2022 American Chemical Society",

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T1 - Visible-Light-Induced Palladium-Catalyzed Cross-Coupling of Iodocarboranes with (Hetero)Arenes

AU - Li, Shimeng

AU - Zhang, Jie

AU - Xie, Zuowei

PY - 2022/10/21

Y1 - 2022/10/21

N2 - This work describes a general method for the efficient production of a class of cage B-centered carboranyl radicals at the B3, B4, and B9 sites via a visible-light-promoted palladium(0)/palladium(I) pathway using readily available iodo-o-carboranes as the starting materials. The electrophilicities of these hypervalent boron-centered radicals decrease in the following order: B3 > B4 > B9. They are useful intermediates for the preparation of a family of cage B-(hetero)arylated o-carboranes at ambient temperature.

AB - This work describes a general method for the efficient production of a class of cage B-centered carboranyl radicals at the B3, B4, and B9 sites via a visible-light-promoted palladium(0)/palladium(I) pathway using readily available iodo-o-carboranes as the starting materials. The electrophilicities of these hypervalent boron-centered radicals decrease in the following order: B3 > B4 > B9. They are useful intermediates for the preparation of a family of cage B-(hetero)arylated o-carboranes at ambient temperature.

UR - https://www.scopus.com/pages/publications/85139548009

U2 - 10.1021/acs.orglett.2c02648

DO - 10.1021/acs.orglett.2c02648

M3 - Journal article

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AN - SCOPUS:85139548009

SN - 1523-7060

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SP - 7497

EP - 7501

JO - Organic Letters

JF - Organic Letters

IS - 41

ER -

Visible-Light-Induced Palladium-Catalyzed Cross-Coupling of Iodocarboranes with (Hetero)Arenes

Abstract

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