Highly Electron-Deficient Dicyanomethylene-Functionalized Triarylboranes with Low-Lying LUMO and Strong Lewis Acidity

Guanming Liao; Xing Chen; Yali Qiao; Kanglei Liu; Nan Wang; Bangkuan Chen; Xiaodong Yin

doi:10.1021/acs.orglett.1c01983

Highly Electron-Deficient Dicyanomethylene-Functionalized Triarylboranes with Low-Lying LUMO and Strong Lewis Acidity

Guanming Liao
, Xing Chen
, Yali Qiao
, Kanglei Liu
, Nan Wang
, Bangkuan Chen^*
, Xiaodong Yin^*

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

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

17 Citations (Scopus)

Abstract

A series of dicyanomethylene-functionalized triarylboranes is reported in this work, with low-lying LUMO energy levels at ca. -3.66 eV for FMesB-ACN. The single-crystal structures of the mono- and dianion of Mes*B-ACN were obtained via chemical reduction, which revealed a conversion from a quinoidal to an aromatic structure. The strong Lewis acidity of these compounds is reflected in a fluoride-anion binding experiment. This work introduces a facile strategy for modulating the electron deficiency of boron-containing compounds.

Original language	English
Pages (from-to)	5836-5841
Number of pages	6
Journal	Organic Letters
Volume	23
Issue number	15
DOIs	https://doi.org/10.1021/acs.orglett.1c01983
Publication status	Published - 6 Aug 2021

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10.1021/acs.orglett.1c01983

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title = "Highly Electron-Deficient Dicyanomethylene-Functionalized Triarylboranes with Low-Lying LUMO and Strong Lewis Acidity",

abstract = "A series of dicyanomethylene-functionalized triarylboranes is reported in this work, with low-lying LUMO energy levels at ca. -3.66 eV for FMesB-ACN. The single-crystal structures of the mono- and dianion of Mes*B-ACN were obtained via chemical reduction, which revealed a conversion from a quinoidal to an aromatic structure. The strong Lewis acidity of these compounds is reflected in a fluoride-anion binding experiment. This work introduces a facile strategy for modulating the electron deficiency of boron-containing compounds.",

author = "Guanming Liao and Xing Chen and Yali Qiao and Kanglei Liu and Nan Wang and Bangkuan Chen and Xiaodong Yin",

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doi = "10.1021/acs.orglett.1c01983",

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T1 - Highly Electron-Deficient Dicyanomethylene-Functionalized Triarylboranes with Low-Lying LUMO and Strong Lewis Acidity

AU - Liao, Guanming

AU - Chen, Xing

AU - Qiao, Yali

AU - Liu, Kanglei

AU - Wang, Nan

AU - Chen, Bangkuan

AU - Yin, Xiaodong

PY - 2021/8/6

Y1 - 2021/8/6

N2 - A series of dicyanomethylene-functionalized triarylboranes is reported in this work, with low-lying LUMO energy levels at ca. -3.66 eV for FMesB-ACN. The single-crystal structures of the mono- and dianion of Mes*B-ACN were obtained via chemical reduction, which revealed a conversion from a quinoidal to an aromatic structure. The strong Lewis acidity of these compounds is reflected in a fluoride-anion binding experiment. This work introduces a facile strategy for modulating the electron deficiency of boron-containing compounds.

AB - A series of dicyanomethylene-functionalized triarylboranes is reported in this work, with low-lying LUMO energy levels at ca. -3.66 eV for FMesB-ACN. The single-crystal structures of the mono- and dianion of Mes*B-ACN were obtained via chemical reduction, which revealed a conversion from a quinoidal to an aromatic structure. The strong Lewis acidity of these compounds is reflected in a fluoride-anion binding experiment. This work introduces a facile strategy for modulating the electron deficiency of boron-containing compounds.

UR - https://www.scopus.com/pages/publications/85111207825

U2 - 10.1021/acs.orglett.1c01983

DO - 10.1021/acs.orglett.1c01983

M3 - Article

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AN - SCOPUS:85111207825

SN - 1523-7060

VL - 23

SP - 5836

EP - 5841

JO - Organic Letters

JF - Organic Letters

IS - 15

ER -

Highly Electron-Deficient Dicyanomethylene-Functionalized Triarylboranes with Low-Lying LUMO and Strong Lewis Acidity

Abstract

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