Synthesis of 3-aryl-1-indanones via CsF-promoted coupling of arylboronic acids with N-tosylhydrazones

被引：6

作者：

Liu, Yueqiang ^{[1
]}

Chen, Lingjuan ^{[1
]}

Liu, Yan ^{[1
]}

Liu, Ping ^{[1
]}

Dai, Bin ^{[1
]}

机构：

[1] Shihezi Univ, Sch Chem & Chem Engn, Key Lab Green Proc Chem Engn Xinjiang Bingtuan, Shihezi City 832004, Peoples R China

来源：

JOURNAL OF CHEMICAL RESEARCH | 2018年 / 01期

基金：

中国国家自然科学基金;

关键词：

3-aryl-1-indanone; 1,3-indanedione; tosylhydrazone; metal-free alkylation; cross-coupling reaction; ONE-POT SYNTHESIS; DIAZO-COMPOUNDS; ASYMMETRIC-SYNTHESIS; CYCLIZATION; HYDROACYLATION; PROTODEBORONATION; DERIVATIVES; ALKYLATION;

D O I：

10.3184/174751918X15161933697844

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A series of 17 3-aryl-1-indanones, four of which are novel, were prepared in good yield via a CsF-promoted reductive cross-coupling of the monotosylhydrazone of a 1,3-indanedione with an arylboronic acid. The method demonstrates wide substrate scope and good functional group tolerance. Moreover, the 3-aryl-1-indanones could also be prepared on a multi-gram scale.

引用

页码：40 / 43

页数：4

共 46 条

[1] Metal-Free Coupling of Saturated Heterocyclic Sulfonylhydrazones with Boronic Acids [J].

Allwood, Daniel M. ;

Blakemore, David C. ;

Brown, Alan D. ;

Ley, Steven V. .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (01) :328-338

[2] Tosylhydrazones: New Uses for Classic Reagents in Palladium-Catalyzed Cross-Coupling and Metal-Free Reactions [J].

Barluenga, Jose ;

Valdes, Carlos .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (33) :7486-7500

[3]

Barluenga J, 2009, NAT CHEM, V1, P494, DOI [10.1038/NCHEM.328, 10.1038/nchem.328]

[4] Gold-Catalyzed Oxidative Cyclizations of cis-3-En-1-ynes To Form Cyclopentenone Derivatives [J].

Bhunia, Sabyasachi ;

Ghorpade, Satish ;

Huple, Deepak B. ;

Liu, Rai-Shung .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (12) :2939-2942

[5]

BOGESO KP, 1988, J MED CHEM, V31, P2247

[6] 3-PHENYL-1-INDANAMINES - POTENTIAL ANTIDEPRESSANT ACTIVITY AND POTENT INHIBITION OF DOPAMINE, NOREPINEPHRINE, AND SEROTONIN UPTAKE [J].

BOGESO, KP ;

CHRISTENSEN, AV ;

HYTTEL, J ;

LILJEFORS, T .

JOURNAL OF MEDICINAL CHEMISTRY, 1985, 28 (12) :1817-1828

[7] REACTIONS IN FUSED ALUMINIUM CHLORIDE-SODIUM CHLORIDE [J].

BRUCE, DB ;

SORRIE, AJS ;

THOMSON, RH .

JOURNAL OF THE CHEMICAL SOCIETY, 1953, (AUG) :2403-2406

[8] Olefination of Carbonyl Compounds through Reductive Coupling of Alkenylboronic Acids and Tosylhydrazones [J].

Carmen Perez-Aguilar, M. ;

Valdes, Carlos .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (24) :5953-5957

[9] Synthesis of indatraline using a Suzuki cross-coupling reaction and a chemoselective hydrogenation: A versatile approach [J].

Cossy, J ;

Belotti, D ;

Magner, A .

SYNLETT, 2003, (10) :1515-1517

[10] Gold(I)-Catalyzed Addition of Silylacetylenes to Acylsilanes: Synthesis of Indanones by CH Functionalization through a Gold(I) Carbenoid [J].

Gonzalez, Jairo ;

Santamaria, Javier ;

Ballesteros, Alfredo .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (46) :13678-13681

← 1 2 3 4 5 →