Synthesis of Dibenzosiloles through Electrocatalytic Sila-Friedel-Crafts Reaction

被引：24

作者：

Han, Pan ^{[1
]}

Yin, Mengyun ^{[1
]}

Li, Haiqiong ^{[1
]}

Yi, Jundan ^{[1
]}

Jing, Linhai ^{[1
]}

Wei, Bangguo ^{[2
]}

机构：

[1] China West Normal Univ, Coll Chem & Chem Engn, Chem Synth & Pollut Control Key Lab Sichuan Prov, 1 Shi Da Rd, Nanchong 637009, Peoples R China

[2] Fudan Univ, Sch Pharm, 826 Zhangheng Rd, Shanghai 201203, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2021年 / 363卷 / 11期

基金：

中国国家自然科学基金;

关键词：

Electrochemical synthesis; C-Si bond construction; Dibenzosiloles; Dehydrogenative coupling;

D O I：

10.1002/adsc.202100262

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A novel electrocatalyzed method for the preparation of dibenzosiloles was developed through intramolecular C-H/Si-H dehydrogenative coupling strategy starting from biarylhydrosilanes. Both electro-donating and electro-withdrawing substitution groups were tolerated for this transformation, and the desired dibenzosilole products could be obtained in moderate to excellent yields. A sila-Friedel-Crafts reaction mechanism was proposed on the basis of previous literature and our controlled experiments.

引用

页码：2757 / 2761

页数：5

共 63 条

[1] Electrophilic Aromatic Substitution with Silicon Electrophiles: Catalytic Friedel-Crafts C-H Silylation [J].

Baehr, Susanne ;

Oestreich, Martin .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (01) :52-59

[2]

Brook M. A., 2000, SILICON ORGANIC ORGA

[3] Poly(2,7-dibenzosilole): A blue light emitting polymer [J].

Chan, KL ;

McKiernan, MJ ;

Towns, CR ;

Holmes, AB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (21) :7662-7663

[4] STRUCTURAL AND CHEMICAL-PROPERTIES OF SILYL RADICALS [J].

CHATGILIALOGLU, C .

CHEMICAL REVIEWS, 1995, 95 (05) :1229-1251

[5] (Me3Si)3SiH:: Twenty years after its discovery as a radical-based reducing agent [J].

Chatgilialoglu, Chryssostomos .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (08) :2310-2320

[6] Recent Applications of the (TMS)3SiH Radical-Based Reagent [J].

Chatgilialoglu, Chryssostomos ;

Lalevee, Jacques .

MOLECULES, 2012, 17 (01) :527-555

[7] A general strategy for the facile synthesis of 2,7-dibromo-9-heterofluorenes [J].

Chen, RF ;

Fan, QL ;

Zheng, C ;

Huang, W .

ORGANIC LETTERS, 2006, 8 (02) :203-205

[8] B(C6F5)3-Catalyzed Synthesis of Benzofused-Siloles [J].

Curless, Liam D. ;

Ingleson, Michael J. .

ORGANOMETALLICS, 2014, 33 (24) :7241-7246

[9] Ethyl 2-Cyano-2-(2-nitrobenzenesulfonyloxyimino) Acetate (ortho-NosylOXY)-Mediated Double Beckmann Rearrangement of Ketoximes under Microwave Irradiation: A Mechanistic Perception [J].

Dev, Dharm ;

Kalita, Tapasi ;

Mondal, Tanmay ;

Mandal, Bhubaneswar .

ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (05) :1427-1435

[10] Application of the sila-Friedel-Crafts reaction to the synthesis of π-extended silole derivatives and their properties [J].

Furukawa, Shunsuke ;

Kobayashi, Junji ;

Kawashima, Takayuki .

DALTON TRANSACTIONS, 2010, 39 (39) :9329-9336

← 1 2 3 4 5 6 7 →