Ir-Catalyzed B(3)-Amination of o-Carboranes with Amines via Acceptorless Dehydrogenative BH/NH Cross-Coupling

Yik Ki Au; Qiangqiang Ma; Jie Zhang; Zuowei Xie

doi:10.1002/asia.202300611

Ir-Catalyzed B(3)-Amination of o-Carboranes with Amines via Acceptorless Dehydrogenative BH/NH Cross-Coupling

Yik Ki Au
, Qiangqiang Ma
, Jie Zhang^*
, Zuowei Xie^*

^*Corresponding author for this work

Department of Chemistry

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

3 Citations (Scopus)

Abstract

An efficient and convenient strategy for Ir-catalyzed selective B(3)-amination of o-carboranes with amines via acceptorless BH/NH dehydrocoupling was developed, affording a series of B(3)-aminated-o-carboranes in moderate to high isolated yields with H₂ gas as a sole by-product. Such an oxidant-free system endues the protocol sustainability, atom-economy and environmental friendliness. A reaction mechanism via an Ir(I)-Ir(III)-Ir(I) catalytic cycle involving oxidative addition, dehydrogenation and reductive elimination was proposed.

Original language	English
Article number	e202300611
Number of pages	5
Journal	Chemistry - An Asian Journal
Volume	18
Issue number	20
Early online date	11 Sept 2023
DOIs	https://doi.org/10.1002/asia.202300611
Publication status	Published - 17 Oct 2023

User-Defined Keywords

amination
B−H activation
carborane
dehydrogenative cross-coupling
regioselectivity

Access to Document

10.1002/asia.202300611

Cite this

@article{d00c491f28eb480b97d201d547b94a5f,

title = "Ir-Catalyzed B(3)-Amination of o-Carboranes with Amines via Acceptorless Dehydrogenative BH/NH Cross-Coupling",

abstract = "An efficient and convenient strategy for Ir-catalyzed selective B(3)-amination of o-carboranes with amines via acceptorless BH/NH dehydrocoupling was developed, affording a series of B(3)-aminated-o-carboranes in moderate to high isolated yields with H2 gas as a sole by-product. Such an oxidant-free system endues the protocol sustainability, atom-economy and environmental friendliness. A reaction mechanism via an Ir(I)-Ir(III)-Ir(I) catalytic cycle involving oxidative addition, dehydrogenation and reductive elimination was proposed.",

keywords = "amination, B−H activation, carborane, dehydrogenative cross-coupling, regioselectivity",

author = "\{Ki Au\}, Yik and Qiangqiang Ma and Jie Zhang and Zuowei Xie",

note = "Funding information: This work was supported by a grant from the Research Grants Council of HKSAR (Project No. 14305420). Publisher Copyright: {\textcopyright} 2023 The Author(s). Chemistry - An Asian Journal published by Wiley-VCH GmbH",

year = "2023",

month = oct,

day = "17",

doi = "10.1002/asia.202300611",

language = "English",

volume = "18",

journal = "Chemistry - An Asian Journal",

issn = "1861-4728",

publisher = "John Wiley \& Sons Ltd",

number = "20",

}

TY - JOUR

T1 - Ir-Catalyzed B(3)-Amination of o-Carboranes with Amines via Acceptorless Dehydrogenative BH/NH Cross-Coupling

AU - Ki Au, Yik

AU - Ma, Qiangqiang

AU - Zhang, Jie

AU - Xie, Zuowei

N1 - Funding information: This work was supported by a grant from the Research Grants Council of HKSAR (Project No. 14305420). Publisher Copyright: © 2023 The Author(s). Chemistry - An Asian Journal published by Wiley-VCH GmbH

PY - 2023/10/17

Y1 - 2023/10/17

N2 - An efficient and convenient strategy for Ir-catalyzed selective B(3)-amination of o-carboranes with amines via acceptorless BH/NH dehydrocoupling was developed, affording a series of B(3)-aminated-o-carboranes in moderate to high isolated yields with H2 gas as a sole by-product. Such an oxidant-free system endues the protocol sustainability, atom-economy and environmental friendliness. A reaction mechanism via an Ir(I)-Ir(III)-Ir(I) catalytic cycle involving oxidative addition, dehydrogenation and reductive elimination was proposed.

AB - An efficient and convenient strategy for Ir-catalyzed selective B(3)-amination of o-carboranes with amines via acceptorless BH/NH dehydrocoupling was developed, affording a series of B(3)-aminated-o-carboranes in moderate to high isolated yields with H2 gas as a sole by-product. Such an oxidant-free system endues the protocol sustainability, atom-economy and environmental friendliness. A reaction mechanism via an Ir(I)-Ir(III)-Ir(I) catalytic cycle involving oxidative addition, dehydrogenation and reductive elimination was proposed.

KW - amination

KW - B−H activation

KW - carborane

KW - dehydrogenative cross-coupling

KW - regioselectivity

UR - https://www.scopus.com/pages/publications/85171635417

U2 - 10.1002/asia.202300611

DO - 10.1002/asia.202300611

M3 - Journal article

C2 - 37694997

AN - SCOPUS:85171635417

SN - 1861-4728

VL - 18

JO - Chemistry - An Asian Journal

JF - Chemistry - An Asian Journal

IS - 20

M1 - e202300611

ER -

Ir-Catalyzed B(3)-Amination of o-Carboranes with Amines via Acceptorless Dehydrogenative BH/NH Cross-Coupling

Abstract

User-Defined Keywords

Access to Document

Other files and links

Fingerprint

Cite this