Metal-Free Selective Borylation of Arenes by a Diazadiborinine via C-H/C-F Bond Activation and Dearomatization

Yuanting Su; Dinh Cao Huan Do; Yongxin Li; Rei Kinjo

doi:10.1021/jacs.9b06022

Metal-Free Selective Borylation of Arenes by a Diazadiborinine via C-H/C-F Bond Activation and Dearomatization

Yuanting Su, Dinh Cao Huan Do, Yongxin Li, Rei Kinjo^*

^*Corresponding author for this work

Nanyang Technological University

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

29 Citations (Scopus)

Abstract

A newly developed annulated 5-chlorinated 1,3,2,5-diazadiborinine derivative (4) selectively activates a C-H bond of benzene (C₆H₆) and 1,3-di(trifluoromethyl)benzene, as well as a C-F bond in partially fluorinated arenes, to furnish borylation products under catalyst-, metal-, and irradiation-free conditions. Moreover, 4 readily undergoes a reversible dearomative coupling reaction with polycyclic aromatic hydrocarbons to afford diboration products. The latter represents the first reversible intermolecular dearomative diboration of arenes.

Original language	English
Pages (from-to)	13729-13733
Number of pages	5
Journal	Journal of the American Chemical Society
Volume	141
Issue number	35
DOIs	https://doi.org/10.1021/jacs.9b06022
Publication status	Published - Sept 4 2019
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2019 American Chemical Society.

ASJC Scopus Subject Areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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title = "Metal-Free Selective Borylation of Arenes by a Diazadiborinine via C-H/C-F Bond Activation and Dearomatization",

abstract = "A newly developed annulated 5-chlorinated 1,3,2,5-diazadiborinine derivative (4) selectively activates a C-H bond of benzene (C6H6) and 1,3-di(trifluoromethyl)benzene, as well as a C-F bond in partially fluorinated arenes, to furnish borylation products under catalyst-, metal-, and irradiation-free conditions. Moreover, 4 readily undergoes a reversible dearomative coupling reaction with polycyclic aromatic hydrocarbons to afford diboration products. The latter represents the first reversible intermolecular dearomative diboration of arenes.",

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T1 - Metal-Free Selective Borylation of Arenes by a Diazadiborinine via C-H/C-F Bond Activation and Dearomatization

AU - Su, Yuanting

AU - Huan Do, Dinh Cao

AU - Li, Yongxin

AU - Kinjo, Rei

PY - 2019/9/4

Y1 - 2019/9/4

N2 - A newly developed annulated 5-chlorinated 1,3,2,5-diazadiborinine derivative (4) selectively activates a C-H bond of benzene (C6H6) and 1,3-di(trifluoromethyl)benzene, as well as a C-F bond in partially fluorinated arenes, to furnish borylation products under catalyst-, metal-, and irradiation-free conditions. Moreover, 4 readily undergoes a reversible dearomative coupling reaction with polycyclic aromatic hydrocarbons to afford diboration products. The latter represents the first reversible intermolecular dearomative diboration of arenes.

AB - A newly developed annulated 5-chlorinated 1,3,2,5-diazadiborinine derivative (4) selectively activates a C-H bond of benzene (C6H6) and 1,3-di(trifluoromethyl)benzene, as well as a C-F bond in partially fluorinated arenes, to furnish borylation products under catalyst-, metal-, and irradiation-free conditions. Moreover, 4 readily undergoes a reversible dearomative coupling reaction with polycyclic aromatic hydrocarbons to afford diboration products. The latter represents the first reversible intermolecular dearomative diboration of arenes.

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Metal-Free Selective Borylation of Arenes by a Diazadiborinine via C-H/C-F Bond Activation and Dearomatization

Abstract

Bibliographical note

ASJC Scopus Subject Areas

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