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

[31] (Thio)urea-catalyzed Friedel-Crafts Reaction: Synthesis of Bis(indolyl)methanes
Rivas-Loaiza, Juan A.
Reyes-Escobedo, Carlos E.
Lopez, Yliana
Rojas-Lima, Susana
Pablo Garcia-Merinos, Juan
Lopez-Ruiz, Heraclio
LETTERS IN ORGANIC CHEMISTRY, 2019, 16 (12) : 959 - 968
[32] Synthesis of indenes by ytterbium-catalyzed carboalkoxylation/Friedel-crafts reaction of arylidenecyclopropanes with acetals
Nakamura, I
Kamada, M
Yamamoto, Y
TETRAHEDRON LETTERS, 2004, 45 (14) : 2903 - 2906
[33] SYNTHESIS OF SIX-MEMBERED FUNCTIONALIZED CARBOCYCLIC COMPOUNDS BY ONE-POT REACTION OF HYDROQUINONE DERIVATIVES AND DIENES
Cai, Guang-Rong
Guan, Zhi
He, Yan-Hong
SYNTHETIC COMMUNICATIONS, 2011, 41 (20) : 3016 - 3025
[34] Synthesis of five- and six-membered lactams via solvent-free microwave Ugi reaction
Jida, Mouhamad
Malaquin, Sandra
Deprez-Poulain, Rebecca
Laconde, Guillaume
Deprez, Benoit
TETRAHEDRON LETTERS, 2010, 51 (39) : 5109 - 5111
[35] Synthesis and Reactivity of Six-Membered Oxa-Nickelacycles: A Ring-Opening Reaction of Cyclopropyl Ketones
Tamaki, Takashi
Nagata, Midue
Ohashi, Masato
Ogoshi, Sensuke
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (39) : 10083 - 10091
[36] AuCl3-Catalyzed Hydroalkoxylation of Conjugated Alkynoates: Synthesis of Five- and Six-Membered Cyclic Acetals
Dieguez-Vazquez, Alejandro
Tzschucke, C. Christoph
Crecente-Campo, Jose
McGrath, Sally
Ley, Steven V.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (11) : 1698 - 1706
[37] Gold-catalyzed C–O bond forming reactions for the synthesis of six-membered O-heterocycles
Navjeet Kaur
Pranshu Bhardwaj
Meenu Devi
Yamini Verma
Pooja Grewal
SN Applied Sciences, 2019, 1
[38] Methods for Metal and Non-Metal Catalyzed Synthesis of Six-Membered Oxygen Containing Poly-Heterocycles
Kaur, Navjeet
CURRENT ORGANIC SYNTHESIS, 2017, 14 (04) : 531 - 556
[39] Intramolecular Pd(II)-Catalyzed Aerobic Oxidative Amination of Alkenes: Synthesis of Six-Membered N-Heterocycles
Lu, Zhan
Stahl, Shannon S.
ORGANIC LETTERS, 2012, 14 (05) : 1234 - 1237
[40] Recent Progress in Iron-Catalyzed Reactions Towards the Synthesis of Bioactive Five- and Six-Membered Heterocycles
Adak, Laksmikanta
Ghosh, Tubai
CURRENT ORGANIC CHEMISTRY, 2020, 24 (22) : 2634 - 2664

← 1 2 3 4 5 →