Gold-Catalyzed Regioselective Remote B(9)–H Activation of <i>o</i> -Carboranes with Silylenynones: Access to B(9)-α-Furylsilyl- <i>o</i> -carboranes

The gold-catalyzed regioselective remote B(9)-H functionalization of <i>o</i>-carboranes through regioselective insertion of <i>α</i>-furyl silyl gold carbenes generated from silylenynones into the B(9)-H bond of <i>o</i>-carboranes offers facile and atom-economical access to various B(9)-<i>α</i>-furylsilyl-<i>o</i>-carboranes in moderate to good yields (up to 88%) with excellent regioselectivities. This method can also be expanded to the selective B-H functionalization of <i>m</i>-carboranes. The synthetic potential of this methodology is exemplified by gram-scale experiments and synthetic transformations of the products.

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Publication Details

Journal
Organic Letters
Published
2026-03-27
DOI
https://doi.org/10.1021/acs.orglett.6c00507
Primary Topic
Boron Compounds in Chemistry
Type
article
Field-Weighted Citation Impact
0.00
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article

Gold-Catalyzed Regioselective Remote B(9)–H Activation of o -Carboranes with Silylenynones: Access to B(9)-α-Furylsilyl- o -carboranes

Yue Hao, Huiyuan Zheng, C Hang, Guanghui Wang et al.
Organic Letters
Boron Compounds in Chemistry
article

Gold-Catalyzed Regioselective Remote B(9)–H Activation of o -Carboranes with Silylenynones: Access to B(9)-α-Furylsilyl- o -carboranes

Yue Hao, Huiyuan Zheng, C Hang, Guanghui Wang, Ximei Zhao, A. Stephen K. Hashmi, Ling Zhi
article en

Abstract

The gold-catalyzed regioselective remote B(9)-H functionalization of <i>o</i>-carboranes through regioselective insertion of <i>α</i>-furyl silyl gold carbenes generated from silylenynones into the B(9)-H bond of <i>o</i>-carboranes offers facile and atom-economical access to various B(9)-<i>α</i>-furylsilyl-<i>o</i>-carboranes in moderate to good yields (up to 88%) with excellent regioselectivities. This method can also be expanded to the selective B-H functionalization of <i>m</i>-carboranes. The synthetic potential of this methodology is exemplified by gram-scale experiments and synthetic transformations of the products.

Organic Letters
Ludong University (CN), Heidelberg University (DE), Analytisches Laboratorium (DE)
Openalex Percentile: Top 6%
Boron Compounds in Chemistry
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