Catalytic Regioselective Cage B(8)–H Arylation of o-Carboranes via “Cage-Walking” Strategy

Hairong Lyu; Jie Zhang; Jingting Yang; Yangjian Quan; Zuowei Xie

doi:10.1021/jacs.9b00302

Catalytic Regioselective Cage B(8)–H Arylation of o-Carboranes via “Cage-Walking” Strategy

Hairong Lyu
, Jie Zhang
, Jingting Yang
, Yangjian Quan^*
, Zuowei Xie^*

^*Corresponding author for this work

Department of Chemistry

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

75 Citations (Scopus)

Abstract

A proof-of-concept example of catalytic regioselective cage B(8)–H functionalization of o-carboranes has been disclosed for the first time. Under the help of an acylamino directing group at cage B(3), a series of B(8)-arylated, B(4,7,8)-triarylated and B(4,7,8)-trifluorinated o-carborane derivatives were conveniently prepared. On the basis of isolation of a key intermediate, deuterium labeling experiments and DFT calculations, a reaction mechanism involving a high-valent palladium induced “cage-walking” from B(4) to B(8) vertex is proposed to account for the regioselective B(8)–H activation.

Original language	English
Pages (from-to)	4219-4224
Number of pages	6
Journal	Journal of the American Chemical Society
Volume	141
Issue number	10
DOIs	https://doi.org/10.1021/jacs.9b00302
Publication status	Published - 13 Mar 2019

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title = "Catalytic Regioselective Cage B(8)–H Arylation of o-Carboranes via “Cage-Walking” Strategy",

abstract = "A proof-of-concept example of catalytic regioselective cage B(8)–H functionalization of o-carboranes has been disclosed for the first time. Under the help of an acylamino directing group at cage B(3), a series of B(8)-arylated, B(4,7,8)-triarylated and B(4,7,8)-trifluorinated o-carborane derivatives were conveniently prepared. On the basis of isolation of a key intermediate, deuterium labeling experiments and DFT calculations, a reaction mechanism involving a high-valent palladium induced “cage-walking” from B(4) to B(8) vertex is proposed to account for the regioselective B(8)–H activation.",

author = "Hairong Lyu and Jie Zhang and Jingting Yang and Yangjian Quan and Zuowei Xie",

note = "Publisher Copyright: {\textcopyright} 2019 American Chemical Society. Funding Information: This work was supported by grants from the Research Grants Council of The Hong Kong Special Administration Region (Project Nos. 14305017, 14305018 and 14305918) and Incentive Fund from Faculty of Science, CUHK.",

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AU - Zhang, Jie

AU - Yang, Jingting

AU - Quan, Yangjian

AU - Xie, Zuowei

N1 - Publisher Copyright: © 2019 American Chemical Society. Funding Information: This work was supported by grants from the Research Grants Council of The Hong Kong Special Administration Region (Project Nos. 14305017, 14305018 and 14305918) and Incentive Fund from Faculty of Science, CUHK.

PY - 2019/3/13

Y1 - 2019/3/13

N2 - A proof-of-concept example of catalytic regioselective cage B(8)–H functionalization of o-carboranes has been disclosed for the first time. Under the help of an acylamino directing group at cage B(3), a series of B(8)-arylated, B(4,7,8)-triarylated and B(4,7,8)-trifluorinated o-carborane derivatives were conveniently prepared. On the basis of isolation of a key intermediate, deuterium labeling experiments and DFT calculations, a reaction mechanism involving a high-valent palladium induced “cage-walking” from B(4) to B(8) vertex is proposed to account for the regioselective B(8)–H activation.

AB - A proof-of-concept example of catalytic regioselective cage B(8)–H functionalization of o-carboranes has been disclosed for the first time. Under the help of an acylamino directing group at cage B(3), a series of B(8)-arylated, B(4,7,8)-triarylated and B(4,7,8)-trifluorinated o-carborane derivatives were conveniently prepared. On the basis of isolation of a key intermediate, deuterium labeling experiments and DFT calculations, a reaction mechanism involving a high-valent palladium induced “cage-walking” from B(4) to B(8) vertex is proposed to account for the regioselective B(8)–H activation.

UR - https://www.scopus.com/pages/publications/85062520510

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JF - Journal of the American Chemical Society

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ER -

Catalytic Regioselective Cage B(8)–H Arylation of o-Carboranes via “Cage-Walking” Strategy

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