Transition-metal-free three-component reaction of cyclopropenes, aldehydes and amines

2016 ◽  
Vol 52 (90) ◽  
pp. 13285-13287 ◽  
Author(s):  
Hang Zhang ◽  
Bo Wang ◽  
Heng Yi ◽  
Tong Sun ◽  
Yan Zhang ◽  
...  
Keyword(s):  
Transition Metal ◽  
Ring Opening ◽  
Metal Free ◽  
Three Component Reaction ◽  
Electron Withdrawing Substituents

A formal [3+2] cycloaddition triggered by enamine-mediated ring-opening of cyclopropenes bearing electron-withdrawing substituents is presented.

Transition-metal free reactions of boronic acids: cascade addition – ring-opening of furans towards functionalized γ-ketoaldehydes

2016 ◽  
Vol 52 (14) ◽  
pp. 3018-3021 ◽  
Author(s):  
S. Roscales ◽  
A. G. Csákÿ
Keyword(s):  
Transition Metal ◽  
Ring Opening ◽  
Boronic Acids ◽  
Metal Free

We describe the first ring-opening of furfuryl alcohols with boronic acids to afford functionalized γ-ketoaldehydes.

scholarly journals Transition-Metal-Free [3+2] Dehydration Cycloaddition of Donor-Acceptor Cyclopropanes With 2-Naphthols

2021 ◽  
Vol 9 ◽  
Author(s):  
Hua Zhao ◽  
Peng Shen ◽  
Dongru Sun ◽  
Hongbin Zhai ◽  
Yufen Zhao
Keyword(s):  
Transition Metal ◽  
Ring Opening ◽  
Metal Catalysts ◽  
Transition Metal Catalysts ◽  
Cyclization Reaction ◽  
Metal Free ◽  
Efficient Access ◽  
Donor Acceptor ◽  
Acid Catalyzed ◽  
Synthetic Application

A Brønsted acid-catalyzed domino ring-opening cyclization transformation of donor-acceptor (D-A) cyclopropanes and 2-naphthols has been developed. This formal [3+2] cyclization reaction provided novel and efficient access to the naphthalene-fused cyclopentanes in the absence of any transition-metal catalysts or additives. This robust procedure was completed smoothly on a gram-scale to afford the corresponding product with comparable efficiency. Furthermore, the synthetic application of the prepared product has been demonstrated by its transformation into a variety of synthetically useful molecules.

Transition-metal-free cleavage of C–C double bonds: a three-component reaction of aromatic alkenes with S8and amides towards aryl thioamides

2018 ◽  
Vol 5 (22) ◽  
pp. 3315-3318 ◽  
Author(s):  
Lantao Liu ◽  
Zhanghong Guo ◽  
Kai Xu ◽  
Shuangshuang Hui ◽  
Xiaofang Zhao ◽  
...  
Keyword(s):  
Transition Metal ◽  
Double Bonds ◽  
Metal Free ◽  
Three Component Reaction

A novel transition-metal-free cleavage of C–C double bonds has been developed from a three-component reaction involving aromatic alkenes, S8and amides, generating various aryl thioamides in up to 96% yields.

scholarly journals Photoinduced successive oxidative ring-opening and borylation of indolizines with NHC–boranes

RSC Advances ◽  
2022 ◽  
Vol 12 (1) ◽  
pp. 470-474
Author(s):  
Huitao Zheng ◽  
Honggang Xiong ◽  
Chaobo Su ◽  
Hua Cao ◽  
Huagang Yao ◽  
...  
Keyword(s):  
Transition Metal ◽  
Ring Opening ◽  
One Pot ◽  
Metal Free

A facile photoinduced successive oxidative ring-opening and borylation of indolizines with NHC–boranes via a one-pot method has been unveiled. This photo-promoted strategy enables the formation of unsaturated NHC–boryl carboxylates under transition metal-free conditions.

Transition-Metal-Free Ring-Opening Silylation of Indoles and Benzofurans with (Diphenyl-tert -butylsilyl)lithium

2017 ◽  
Vol 56 (44) ◽  
pp. 13872-13875 ◽  
Author(s):  
Pan Xu ◽  
Ernst-Ulrich Würthwein ◽  
Constantin G. Daniliuc ◽  
Armido Studer
Keyword(s):  
Transition Metal ◽  
Ring Opening ◽  
Free Ring ◽  
Metal Free

Transition-Metal-Free Three-Component Reaction: Additive Controlled Synthesis of Sulfonylated Imidazoles

2019 ◽  
Vol 84 (17) ◽  
pp. 11348-11358 ◽  
Author(s):  
Wei Liu ◽  
Yu Zhang ◽  
Jiaming He ◽  
Yue Yu ◽  
Jiajun Yuan ◽  
...  
Keyword(s):  
Transition Metal ◽  
Controlled Synthesis ◽  
Metal Free ◽  
Three Component Reaction

Direct synthesis of ortho-methylthio allyl and vinyl ethers via three component reaction of aryne, activated alkene and DMSO

2020 ◽  
Vol 18 (14) ◽  
pp. 2727-2738 ◽  
Author(s):  
Hemanta Hazarika ◽  
Pranjal Gogoi
Keyword(s):  
Transition Metal ◽  
Direct Synthesis ◽  
Vinyl Ethers ◽  
Metal Free ◽  
Synthetic Strategy ◽  
Three Component Reaction ◽  
Three Component Coupling

A transition-metal free synthetic strategy for the direct synthesis of ortho-methylthio allyl and vinyl ethers via cascade three-component coupling of aryne, activated alkene and DMSO.

Sonication and Microwave-Assisted Primary Amination of Potassium­ Aryltrifluoroborates and Phenylboronic Acids under Metal-Free Conditions

Synthesis ◽  
2017 ◽  
Vol 49 (11) ◽  
pp. 2555-2561 ◽  
Author(s):  
Dale Kuik ◽  
J. McCubbin ◽  
Geoffrey Tranmer
Keyword(s):  
Transition Metal ◽  
Reaction Times ◽  
Aqueous Sodium Hydroxide ◽  
Metal Free ◽  
Microwave Assisted ◽  
Free Generation ◽  
Phenylboronic Acids ◽  
Microwave Assisted Method ◽  
General Method ◽  
Electron Withdrawing Substituents

The transition-metal-free generation of a series of primary arylamines from potassium aryltrifluoroborates and phenylboronic acids­ is reported. The method uses a mild, inexpensive source of nitrogen (hydroxylamine-O-sulfonic acid) in cooperation with aqueous sodium hydroxide in acetonitrile. Both a sonication and a microwave-assisted method were developed, which are capable of converting ArBF3K functionalities into primary arylamines (ArNH2) in isolated yields of up to 78% (10 examples for each method). This report represents the first general method for the conversion of aryltrifluoroborates into primary arylamines under mild, transition-metal-free conditions in moderate to very good yields. The method is applicable to a wide array of substrates containing electron-donating, electron-neutral, or electron-withdrawing substituents. Both the sonication and microwave methods were also applied to the generation of anilines from phenylboronic acids in isolated yields of up to 96% (12 examples for each method) that were superior to existing room temperature methods in terms of yield, while also offering much shorter reaction times (15 min vs 16 h). In particular, the microwave method is the first to allow for the conversion of arylboronic acids containing strongly electron-withdrawing substituents into the corresponding anilines in good yields, along with electron-donating­ substituents in very good to excellent yields.

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