Palladium-Catalyzed Asymmetric B–H Arylation of o-Carboranes Assisted by a Chiral Transient Directing Group

Yanglong Zou; Jie Zhang; Wei Hong; Dengsong Zhang; Zaozao Qiu; Zuowei Xie

doi:10.1021/acscatal.5c08932

Palladium-Catalyzed Asymmetric B–H Arylation of o-Carboranes Assisted by a Chiral Transient Directing Group

Yanglong Zou
, Jie Zhang
, Wei Hong
, Dengsong Zhang
, Zaozao Qiu^*
, Zuowei Xie^*

^*Corresponding author for this work

Department of Chemistry

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

1 Citation (Scopus)

Abstract

Chiral-at-cage o-carboranes represent a class of three-dimensional boron-cluster-based chiral molecules. Herein, we report a Pd-catalyzed regio- and enantioselective B(4)–H arylation of o-carboranyl benzaldehydes enabled by a chiral transient directing group (cTDG) strategy using l-threonine. The reaction proceeds via reversible imine formation and enantioselective B–H arylation, affording chiral-at-cage products in up to 87% yield and 98% ee. Chiroptical characterizations confirm the potential of the products in optoelectronic materials. This work provides a practical approach to asymmetric B–H functionalization using in-situ-formed cTDGs.

Original language	English
Pages (from-to)	4951-4960
Number of pages	10
Journal	ACS Catalysis
Volume	16
Issue number	5
Early online date	24 Feb 2026
DOIs	https://doi.org/10.1021/acscatal.5c08932
Publication status	Published - 6 Mar 2026

UN SDGs

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

SDG 9 Industry, Innovation, and Infrastructure

User-Defined Keywords

arylation
asymmetric B−H bond activation
cage chirality
carborane
chiral-at-cage
transient directing group

Access to Document

10.1021/acscatal.5c08932

Cite this

@article{b8ac09561a2448d9a155d7df75713604,

title = "Palladium-Catalyzed Asymmetric B–H Arylation of o-Carboranes Assisted by a Chiral Transient Directing Group",

abstract = "Chiral-at-cage o-carboranes represent a class of three-dimensional boron-cluster-based chiral molecules. Herein, we report a Pd-catalyzed regio- and enantioselective B(4)–H arylation of o-carboranyl benzaldehydes enabled by a chiral transient directing group (cTDG) strategy using l-threonine. The reaction proceeds via reversible imine formation and enantioselective B–H arylation, affording chiral-at-cage products in up to 87\% yield and 98\% ee. Chiroptical characterizations confirm the potential of the products in optoelectronic materials. This work provides a practical approach to asymmetric B–H functionalization using in-situ-formed cTDGs.",

keywords = "arylation, asymmetric B−H bond activation, cage chirality, carborane, chiral-at-cage, transient directing group",

author = "Yanglong Zou and Jie Zhang and Wei Hong and Dengsong Zhang and Zaozao Qiu and Zuowei Xie",

note = "This work was supported by grants from the National Natural Science Foundation of China (Project No. 22371290 and 92056106 to Z. Q.; Project No. 22331005 to Z. X.), the Shenzhen Science and Technology Program (Project No. KQTD20221101093558015 to Z. X.), the Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, CAS, and the Hong Kong Research Grants Council (Project No. JLFS/P- 404/24). Publisher Copyright: {\textcopyright} 2026 American Chemical Society",

year = "2026",

month = mar,

day = "6",

doi = "10.1021/acscatal.5c08932",

language = "English",

volume = "16",

pages = "4951--4960",

journal = "ACS Catalysis",

issn = "2155-5435",

publisher = "American Chemical Society",

number = "5",

}

TY - JOUR

T1 - Palladium-Catalyzed Asymmetric B–H Arylation of o-Carboranes Assisted by a Chiral Transient Directing Group

AU - Zou, Yanglong

AU - Zhang, Jie

AU - Hong, Wei

AU - Zhang, Dengsong

AU - Qiu, Zaozao

AU - Xie, Zuowei

N1 - This work was supported by grants from the National Natural Science Foundation of China (Project No. 22371290 and 92056106 to Z. Q.; Project No. 22331005 to Z. X.), the Shenzhen Science and Technology Program (Project No. KQTD20221101093558015 to Z. X.), the Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, CAS, and the Hong Kong Research Grants Council (Project No. JLFS/P- 404/24). Publisher Copyright: © 2026 American Chemical Society

PY - 2026/3/6

Y1 - 2026/3/6

N2 - Chiral-at-cage o-carboranes represent a class of three-dimensional boron-cluster-based chiral molecules. Herein, we report a Pd-catalyzed regio- and enantioselective B(4)–H arylation of o-carboranyl benzaldehydes enabled by a chiral transient directing group (cTDG) strategy using l-threonine. The reaction proceeds via reversible imine formation and enantioselective B–H arylation, affording chiral-at-cage products in up to 87% yield and 98% ee. Chiroptical characterizations confirm the potential of the products in optoelectronic materials. This work provides a practical approach to asymmetric B–H functionalization using in-situ-formed cTDGs.

AB - Chiral-at-cage o-carboranes represent a class of three-dimensional boron-cluster-based chiral molecules. Herein, we report a Pd-catalyzed regio- and enantioselective B(4)–H arylation of o-carboranyl benzaldehydes enabled by a chiral transient directing group (cTDG) strategy using l-threonine. The reaction proceeds via reversible imine formation and enantioselective B–H arylation, affording chiral-at-cage products in up to 87% yield and 98% ee. Chiroptical characterizations confirm the potential of the products in optoelectronic materials. This work provides a practical approach to asymmetric B–H functionalization using in-situ-formed cTDGs.

KW - arylation

KW - asymmetric B−H bond activation

KW - cage chirality

KW - carborane

KW - chiral-at-cage

KW - transient directing group

UR - https://www.scopus.com/pages/publications/105031906098

UR - https://pubs.acs.org/doi/10.1021/acscatal.5c08932

U2 - 10.1021/acscatal.5c08932

DO - 10.1021/acscatal.5c08932

M3 - Journal article

AN - SCOPUS:105031906098

SN - 2155-5435

VL - 16

SP - 4951

EP - 4960

JO - ACS Catalysis

JF - ACS Catalysis

IS - 5

ER -

Palladium-Catalyzed Asymmetric B–H Arylation of o-Carboranes Assisted by a Chiral Transient Directing Group

Abstract

UN SDGs

User-Defined Keywords

Access to Document

Other files and links

Fingerprint

Cite this