Regioselective insertion of carborynes into ethereal C-H bond: Facile synthesis of α-carboranylated ethers

Sunewang R. Wang; Zaozao Qiu; Zuowei Xie

doi:10.1021/ja201126h

Regioselective insertion of carborynes into ethereal C-H bond: Facile synthesis of α-carboranylated ethers

Sunewang R. Wang
, Zaozao Qiu
, Zuowei Xie^*

^*Corresponding author for this work

Chinese University of Hong Kong

Research output: Contribution to journal › Article › peer-review

47 Scopus citations

Abstract

Carborynes can exist in two resonance forms, bonding form vs biradical form. The biradical form can be readily generated via the elimination of LiI from 1-iodo-n-lithio-1,n-C₂B₁₀H₁₀ (n = 2, 7) under UV irradiation. They can undergo α-C-H bond insertion with aliphatic ethers, affording α-carboranylated ethers in excellent regioselectivity at room temperature. This serves as a new methodology for the generation of a series of functionalized carboranes bearing alkoxy units.

Original language	English
Pages (from-to)	5760-5763
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	133
Issue number	15
DOIs	https://doi.org/10.1021/ja201126h
State	Published - 20 Apr 2011
Externally published	Yes

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title = "Regioselective insertion of carborynes into ethereal C-H bond: Facile synthesis of α-carboranylated ethers",

abstract = "Carborynes can exist in two resonance forms, bonding form vs biradical form. The biradical form can be readily generated via the elimination of LiI from 1-iodo-n-lithio-1,n-C2B10H10 (n = 2, 7) under UV irradiation. They can undergo α-C-H bond insertion with aliphatic ethers, affording α-carboranylated ethers in excellent regioselectivity at room temperature. This serves as a new methodology for the generation of a series of functionalized carboranes bearing alkoxy units.",

author = "Wang, \{Sunewang R.\} and Zaozao Qiu and Zuowei Xie",

year = "2011",

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doi = "10.1021/ja201126h",

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T2 - Facile synthesis of α-carboranylated ethers

AU - Wang, Sunewang R.

AU - Qiu, Zaozao

AU - Xie, Zuowei

PY - 2011/4/20

Y1 - 2011/4/20

N2 - Carborynes can exist in two resonance forms, bonding form vs biradical form. The biradical form can be readily generated via the elimination of LiI from 1-iodo-n-lithio-1,n-C2B10H10 (n = 2, 7) under UV irradiation. They can undergo α-C-H bond insertion with aliphatic ethers, affording α-carboranylated ethers in excellent regioselectivity at room temperature. This serves as a new methodology for the generation of a series of functionalized carboranes bearing alkoxy units.

AB - Carborynes can exist in two resonance forms, bonding form vs biradical form. The biradical form can be readily generated via the elimination of LiI from 1-iodo-n-lithio-1,n-C2B10H10 (n = 2, 7) under UV irradiation. They can undergo α-C-H bond insertion with aliphatic ethers, affording α-carboranylated ethers in excellent regioselectivity at room temperature. This serves as a new methodology for the generation of a series of functionalized carboranes bearing alkoxy units.

UR - https://www.scopus.com/pages/publications/79954500075

U2 - 10.1021/ja201126h

DO - 10.1021/ja201126h

M3 - 文章

AN - SCOPUS:79954500075

SN - 0002-7863

VL - 133

SP - 5760

EP - 5763

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 15

ER -

Regioselective insertion of carborynes into ethereal C-H bond: Facile synthesis of α-carboranylated ethers

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