scholarly journals Oxidative Dearomative Cross-Dehydrogenative Coupling of Indoles with Diverse C-H Nucleophiles: Efficient Approach to 2,2-Disubstituted Indolin-3-ones

Molecules ◽  
2020 ◽  
Vol 25 (2) ◽  
pp. 419 ◽  
Author(s):  
Xue Yan ◽  
Ying-De Tang ◽  
Cheng-Shi Jiang ◽  
Xigong Liu ◽  
Hua Zhang
Keyword(s):  
Oxidative Dimerization ◽  
Efficient Approach ◽  
Dehydrogenative Coupling ◽  
High Yields

The oxidative, dearomative cross-dehydrogenative coupling of indoles with various C-H nucleophiles is developed. This process features a broad substrate scope with respect to both indoles and nucleophiles, affording structurally diverse 2,2-disubstituted indolin-3-ones in high yields (up to 99%). The oxidative dimerization and trimerization of indoles has also been demonstrated under the same conditions.

scholarly journals Synthesis of N-alkoxyphthalimide derivatives via PIDA-promoted cross dehydrogenative coupling reaction

RSC Advances ◽  
2021 ◽  
Vol 11 (14) ◽  
pp. 8051-8054
Author(s):  
Rongxiang Chen ◽  
Bing Liu ◽  
Wenbo Li ◽  
Kai-Kai Wang ◽  
Changqing Miao ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Dehydrogenative Coupling ◽  
Aryl Ketones ◽  
High Yields

A cross dehydrogenative coupling reaction of aryl ketones with N-hydroxyphthalimide was realized. The reactions afforded a clean and facile access to diverse N-alkoxyphthalimide derivatives in high yields (up to 99%).

scholarly journals Efficient synthesis of pyrazolopyridines containing a chromane backbone through domino reaction

2019 ◽  
Vol 15 ◽  
pp. 874-880
Author(s):  
Razieh Navari ◽  
Saeed Balalaie ◽  
Saber Mehrparvar ◽  
Fatemeh Darvish ◽  
Frank Rominger ◽  
...  
Keyword(s):  
Room Temperature ◽  
High Selectivity ◽  
Domino Reaction ◽  
Primary Amines ◽  
Efficient Synthesis ◽  
Atom Economy ◽  
Reaction Conditions ◽  
Efficient Approach ◽  
Three Component Reaction ◽  
High Yields

An efficient approach for the synthesis of pyrazolopyridines containing the aminochromane motif through a base-catalyzed cyclization reaction is reported. The synthesis was carried out through a three-component reaction of (arylhydrazono)methyl-4H-chromen-4-one, malononitrile, primary amines in the presence of Et3N at room temperature. However, carrying out the reaction under the same conditions without base led to a fused chromanyl-cyanopyridine. High selectivity, high atom economy, and good to high yields in addition to mild reaction conditions are the advantages of this approach.

Palladium-catalyzed dehydrogenative coupling of terminal alkynes with secondary phosphine oxides

2015 ◽  
Vol 51 (17) ◽  
pp. 3549-3551 ◽  
Author(s):  
Jia Yang ◽  
Tieqiao Chen ◽  
Yongbo Zhou ◽  
Shuangfeng Yin ◽  
Li-Biao Han
Keyword(s):  
Reaction Mechanism ◽  
Palladium Acetate ◽  
Secondary Phosphine ◽  
Terminal Alkynes ◽  
Phosphine Oxides ◽  
Dehydrogenative Coupling ◽  
Palladium Catalyzed ◽  
High Yields

The palladium-catalyzed dehydrogenative coupling of alkynes with secondary phosphine oxides is developed. Thus, in the presence of a silver additive, palladium acetate could efficiently catalyze the dehydrocoupling of secondary phosphine oxides with a variety of alkynes to produce the corresponding alkynylphosphine oxides in high yields. A reaction mechanism is proposed.

Catalyst-free direct cross-dehydrogenative coupling of imidazoheterocycles with glyoxal hydrates: an efficient approach to 1,2-diketones

2019 ◽  
Vol 17 (12) ◽  
pp. 3150-3158 ◽  
Author(s):  
Tao Guo ◽  
Xiang-Heng Fu ◽  
Miao Zhang ◽  
Yu-Liu Li ◽  
Yong-Cheng Ma
Keyword(s):  
Efficient Approach ◽  
Catalyst Free ◽  
Dehydrogenative Coupling ◽  
Direct Cross

An efficient and convenient catalyst-free synthesis of 1,2-diketones via cross-dehydrogenative coupling of imidazoheterocycles with glyoxal hydrates is described.

Iron(ii)-catalyzed C-2 cyanomethylation of indoles and pyrroles via direct oxidative cross-dehydrogenative coupling with acetonitrile derivatives

2018 ◽  
Vol 5 (7) ◽  
pp. 1129-1134 ◽  
Author(s):  
Kai Qiao ◽  
Dong Zhang ◽  
Kai Zhang ◽  
Xin Yuan ◽  
Ming-Wei Zheng ◽  
...  
Keyword(s):  
Oxidative Coupling ◽  
Efficient Approach ◽  
Dehydrogenative Coupling

A novel and efficient approach for the C(sp2)–H/C(sp3)–H oxidative coupling of indoles and pyrroles with acetonitrile derivatives was reported by using the Fe(ii) complex.

Palladium Catalyzed Cross -Dehydrogenative Coupling/Annulation Reaction: A Practical and Efficient Approach to Hydroxyisoindolo[1,2-b ]quinazolinone

2019 ◽  
Vol 2019 (18) ◽  
pp. 2933-2940 ◽  
Author(s):  
Minoo Dabiri ◽  
Noushin Farajinia Lehi ◽  
Siyavash Kazemi Movahed ◽  
Hamid Reza Khavasi
Keyword(s):  
Efficient Approach ◽  
Dehydrogenative Coupling ◽  
Palladium Catalyzed

scholarly journals A novel application of 2-silylated 1,3-dithiolanes for the synthesis of aryl/hetaryl-substituted ethenes and dibenzofulvenes

2017 ◽  
Vol 13 ◽  
pp. 1900-1906 ◽  
Author(s):  
Grzegorz Mlostoń ◽  
Paulina Pipiak ◽  
Róża Hamera-Fałdyga ◽  
Heinz Heimgartner
Keyword(s):  
Equimolar Amount ◽  
One Pot ◽  
Efficient Approach ◽  
Highly Efficient ◽  
High Yields

Trimethylsilyldiazomethane (TMS-CHN2) reacts readily with hetaryl thioketones to give sterically crowded 2-trimethylsilyl-4,4,5,5-tetrahetaryl-1,3-dithiolanes with complete regioselectivity at −75 °C as well as at rt. Thiofluorenone, a relatively stable and highly reactive aryl thioketone, yields upon treatment with TMS-CHN2 at −60 °C the corresponding 1,3,4-thiadiazoline. This unstable cycloadduct undergoes decomposition at ca. −45 °C and the silylated thiocarbonyl S-methanide generated thereby is trapped with complete regioselectivity by aryl or hetaryl thioketones forming also sterically crowded 2-trimethylsilyl-1,3-dithiolanes. The obtained 1,3-dithiolanes, by treatment with an equimolar amount of TBAF in a one-pot procedure, are converted in high yields into hetaryl/aryl-substituted ethenes or dibenzofulvenes, respectively, via a cycloreversion reaction of the intermediate 1,3-dithiolane carbanion. The presented protocol offers a new, highly efficient approach to tetrasubstituted ethenes and dibenzofulvenes bearing aryl and/or hetaryl substituents.

scholarly journals DOWEX(R)50WX4/H2O: A Green System for a One-pot and Three-Component Synthesis of isoxazol-5(4H)-one Derivatives

2017 ◽  
Vol 59 (3) ◽  
Author(s):  
Davood Setamdideh
Keyword(s):  
Present Method ◽  
Reaction Times ◽  
One Pot ◽  
Efficient Approach ◽  
High Yields ◽  
Green System ◽  
Reaction Profile ◽  
Operational Simplicity

A one-pot and three-component synthesis of 3-methyl-4-arylmethyleneisoxazol-5(4<em>H</em>)-ones was developed in the presence of DOWEX(R)50WX4 as the catalyst. The products were obtained in high yields (93-96%) and short reaction times (30-60 min). The present method provides an easy and efficient approach for the synthesis of this class of compounds, because of its clean reaction profile and operational simplicity.

Copper-Mediated One-Pot Synthesis of Indoles through Sequential Hydroamination and Cross-Dehydrogenative Coupling Reaction

Synthesis ◽  
2019 ◽  
Vol 52 (01) ◽  
pp. 75-84 ◽  
Author(s):  
Peng Sun ◽  
Jiaojiao Yang ◽  
Zirui Song ◽  
Yichao Cai ◽  
Yajie Liu ◽  
...  
Keyword(s):  
Mixed Solvents ◽  
Coupling Reaction ◽  
One Pot ◽  
One Pot Synthesis ◽  
Dehydrogenative Coupling ◽  
High Yields

Starting from simple anilines and ester arylpropiolates, an efficient one-pot synthesis of 2-arylindole-3-carboxylate derivatives has been developed through copper-mediated sequential hydroamination and cross-dehydrogenative coupling (CDC) reaction. The initial hydroamination of anilines to ester arylpropiolates in benzene can proceed in a stereoselective manner to give ester (Z)-3-(arylamino)acrylates in the presence of CuCl2/phenanthroline, KMnO4, and KHCO3 at 120 °C. Sequentially, these in situ functionalized adducts can undergo direct intramolecular oxidative alkenylation of aromatic C–H bond in mixed solvents (benzene/DMSO 1:1) at 130 °C affording multi-substituted­ indoles in good to high yields.

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