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

22 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

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 9 Industry, Innovation, and Infrastructure

Access to Document

10.1021/acs.orglett.2c02648

Cite this

@article{e336dff5bc364a4d9b701350f9c68d48,

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",

year = "2022",

month = oct,

day = "21",

doi = "10.1021/acs.orglett.2c02648",

language = "English",

volume = "24",

pages = "7497--7501",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "41",

}

TY - JOUR

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

C2 - 36201284

AN - SCOPUS:85139548009

SN - 1523-7060

VL - 24

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

UN SDGs

Access to Document

Other files and links

Fingerprint

Cite this