Synthesis of six-membered silacycles by borane-catalyzed double sila-Friedel-Crafts reaction

被引：6

作者：

Dong, Yafang ^{[1
]}

Sakai, Masahiko ^{[1
]}

Fuji, Kazuto ^{[1
]}

Sekine, Kohei ^{[1
,2
]}

Kuninobu, Yoichiro ^{[1
,2
]}

机构：

[1] Kyushu Univ, Interdisciplinary Grad Sch Engn Sci, 6-1 Kasugakoen, Kasuga, Fukuoka 8168580, Japan

[2] Kyushu Univ, Inst Mat Chem & Engn, 6-1 Kasugakoen, Kasuga, Fukuoka 8168580, Japan

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 16卷

关键词：

borane; cyclic compound; organosilane; sila-Friedel-Crafts; silylation; BITE ANGLE; DERIVATIVES; LIGANDS; HYDROFORMYLATION; PHENAZASILINES; ATROPISOMERISM; PHENOXASILIN; SILYLATION; CLEAVAGE;

D O I：

10.3762/bjoc.16.39

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have developed a catalytic synthetic method to prepare phenoxasilins. A borane-catalyzed double sila-Friedel-Crafts reaction between amino group-containing diaryl ethers and dihydrosilanes can be used to prepare a variety of phenoxasilin derivatives in good to excellent yields. The optimized reaction conditions were also applicable for diaryl thioethers to afford their corresponding six-membered silacyclic products. The gram-scale synthesis of a representative bis(dimethylamino)phenoxasilin and the transformation of its amino groups have also been demonstrated.

引用

页码：409 / 414

页数：6

共 50 条

[1] Synthesis of Dibenzosiloles through Electrocatalytic Sila-Friedel-Crafts Reaction
Han, Pan
Yin, Mengyun
Li, Haiqiong
Yi, Jundan
Jing, Linhai
Wei, Bangguo
ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (11) : 2757 - 2761
[2] Synthesis of Six-Membered Silacycles
Liu Junhui
Zhang Shaoguang
Zhang Wenxiong
Xi Zhenfeng
PROGRESS IN CHEMISTRY, 2009, 21 (7-8) : 1475 - 1486
[3] Application of the sila-Friedel-Crafts reaction to the synthesis of π-extended silole derivatives and their properties
Furukawa, Shunsuke
Kobayashi, Junji
Kawashima, Takayuki
DALTON TRANSACTIONS, 2010, 39 (39) : 9329 - 9336
[4] Lewis acid-catalyzed synthesis of silafluorene derivatives from biphenyls and dihydrosilanes via a double sila-Friedel-Crafts reaction
Dong, Yafang
Takata, Yuta
Yoshigoe, Yusuke
Sekine, Kohei
Kuninobu, Yoichiro
CHEMICAL COMMUNICATIONS, 2019, 55 (88) : 13303 - 13306
[5] Development of a Sila-Friedel-Crafts Reaction and Its Application to the Synthesis of Dibenzosilole Derivatives
Furukawa, Shunsuke
Kobayashi, Junji
Kawashima, Takayuki
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (40) : 14192 - +
[6] Utilization of Borane-Catalyzed Hydrosilylation as a Dearomatizing Tool: Six-Membered Cyclic Amidine Synthesis from Isoquinolines and Pyridines
Cao, Vinh Do
Jo, Dong Geun
Kim, Huiae
Kim, Changeun
Yun, Seula
Joung, Seewon
SYNTHESIS-STUTTGART, 2021, 53 (04): : 754 - 764
[7] Synthesis of six-membered spirooxindoles via a chiral Bronsted acid-catalyzed asymmetric intramolecular Friedel-Crafts reaction
Chen, Hui-Xuan
Zhang, Yaqi
Zhang, Yuyang
He, Xuefeng
Zhang, Zhen-Wei
Liang, Hao
He, Wenhuan
Jiang, Xiaoding
Chen, Xiangmeng
Qiu, Liqin
RSC ADVANCES, 2018, 8 (65): : 37035 - 37039
[8] Prins-Friedel-Crafts Cyclization: Synthesis of Diversely Functionalized Six-Membered Oxacycles
Roy, Snigdha
CURRENT ORGANIC CHEMISTRY, 2021, 25 (05) : 635 - 651
[9] An Overview of Ag-catalyzed Synthesis of Six-membered Heterocycles
Neetha, Mohan
Aneeja, Thaipparambil
Afsina, C. M. A.
Anilkumar, Gopinathan
CHEMCATCHEM, 2020, 12 (21) : 5330 - 5358
[10] Synthesis of Six-membered Silacycles by Intramolecular Nucleophilic Substitution at Silicon Involving the Cleavage of Carbon-Silicon Bonds
Onoe, Masahiro
Morioka, Toshifumi
Tobisu, Mamoru
Chatani, Naoto
CHEMISTRY LETTERS, 2013, 42 (03) : 238 - 240

← 1 2 3 4 5 →