Fluorination/Dearomatization of C6F5 Groups: An FLP Route to an Electrophilic Borane and Non-Coordinating Anions

被引：1

作者：

Kim, Hyehwang ^{[1
]}

Mandal, Dipendu ^{[1
,3
]}

Ng, Joshua Kye Jin ^{[1
]}

Qu, Zheng-Wang ^{[2
]}

Grimme, Stefan ^{[2
]}

Stephan, Douglas W. ^{[1
,3
]}

机构：

[1] Univ Toronto, Dept Chem, 80 St George St, Toronto, ON M5S 3H6, Canada

[2] Rhein Friedrich Wilhelms Univ Bonn, Clausius Inst Phys & Theoret Chem, Mulliken Ctr Theoret Chem, Beringstr 4, D-53115 Bonn, Germany

[3] Ningbo Univ, Inst Drug Discovery Technol, Ningbo 315211, Zhejiang, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2024年 / 30卷 / 43期

基金：

加拿大自然科学与工程研究理事会;

关键词：

fluorination; borane adducts; borate salts; septafluorohexadienyl substituents; frustrated Lewis pairs; ZETA-VALENCE QUALITY; XENON DIFLUORIDE; BASIS-SETS; STRUCTURAL-CHARACTERIZATION; HYDROGEN-FLUORIDE; FLUORINATION; PHOSPHINES; REACTIVITY; CHEMISTRY; CATALYSIS;

D O I：

10.1002/chem.202401776

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

B(C6F5)(3) and the corresponding anion [B(C6F5)(4)](-) are ubiquitous in main group and transition metal chemistry. Known derivatives are generally limited to the incorporation of electron donating substituents. Herein we describe electrophilic fluorination and dearomatization of such species using XeF2 in the presence of BF3 or Lewis acidic cations. In this fashion the anions [HB(C6F5)(3)](-), [B(C6F5)(4)](-) and [(C6F5)(3)BC equivalent to NB(C6F5)(3)](-), are converted to [FB(C6F7)(3)](-), [B(C6F7)(4)](-), and [(C6F7)(3)BC equivalent to NB(C6F7)(3)](-), respectively. Similarly, the borane adducts (L)B(C6F7)(3) (L=MeCN, OPEt3) are produced. These rare examples of electrophilic attack of electron deficient rings proceed as [XeF][BF4] acts as a frustrated Lewis pair effecting fluorination and dearomatization of C6F5 rings.

引用

页数：5

共 30 条

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