C3 functionalization of indolizines via In(iii)-catalyzed three-component reaction

2015 ◽  
Vol 13 (45) ◽  
pp. 10986-10994 ◽  
Author(s):  
Youngeun Jung ◽  
Ikyon Kim
Keyword(s):  
Functional Groups ◽  
Coupling Reaction ◽  
New Class ◽  
Rapid Access ◽  
Three Component Reaction ◽  
Post Functionalization ◽  
Three Component Coupling

Post-functionalization at the C3 position of indolizines via In(iii)-catalyzed three-component coupling reaction with amines and aldehydes allowed rapid access to a new class of indolizines with diverse functional groups at the C3 position in good to excellent yields.

scholarly journals K2S2O8-Promoted Aryl Thioamides Synthesis from Aryl Aldehydes Using Thiourea as the Sulfur Source

Molecules ◽  
2018 ◽  
Vol 23 (9) ◽  
pp. 2225 ◽  
Author(s):  
Yongjun Bian ◽  
Xingyu Qu ◽  
Yongqiang Chen ◽  
Jun Li ◽  
Leng Liu
Keyword(s):  
Transition Metal ◽  
Functional Groups ◽  
Sulfur Atom ◽  
Coupling Reaction ◽  
Sulfur Source ◽  
Atom Transfer ◽  
Free Condition ◽  
Metal Free ◽  
Aryl Aldehydes ◽  
Three Component Coupling

Thiourea as a sulfur atom transfer reagent was applied for the synthesis of aryl thioamides through a three-component coupling reaction with aryl aldehydes and N,N-dimethylformamide (DMF) or N,N-dimethylacetamide (DMAC). The reaction could tolerate various functional groups and gave moderate to good yields of desired products under the transition-metal-free condition.

A bromine-radical mediated three-component reaction comprising allenes, electron-deficient alkenes and allyl bromides: facile synthesis of 2-bromo-1,7-dienes

2014 ◽  
Vol 50 (45) ◽  
pp. 5993-5996 ◽  
Author(s):  
Takashi Kippo ◽  
Ilhyong Ryu
Keyword(s):  
Coupling Reaction ◽  
Facile Synthesis ◽  
Three Component Reaction ◽  
High Yields ◽  
Three Component Coupling

A bromine-radical mediated three-component coupling reaction was effectively achieved by the use of allenes, electron-deficient alkenes, and allyl bromides and led to the synthesis of 2-bromo-1,7-dienes in good to high yields.

scholarly journals N-Alkylation/aldol reaction of α-aldimino thioesters: a facile three-component coupling reaction

RSC Advances ◽  
2021 ◽  
Vol 11 (22) ◽  
pp. 13097-13104
Author(s):  
Makoto Shimizu ◽  
Asako Higashino ◽  
Isao Mizota ◽  
Yusong Zhu
Keyword(s):  
Aldol Reaction ◽  
Coupling Reaction ◽  
Three Component Coupling

Treatment of α-aldimino thioesters with dialkylzinc reagents in the presence of aldehydes or imines gives three-component coupling products in good yields with good to high anti-selectivities.

Visible-light-induced remote C(sp3)-H sulfonylvinylation: assembly of cyanoalkylated vinyl sulfones

2021 ◽  
Author(s):  
Ping Bao ◽  
Feiyan Yu ◽  
Fu-Sheng He ◽  
Zhimei Tang ◽  
Wei-Ping Deng ◽  
...  
Keyword(s):  
Visible Light ◽  
Rapid Access ◽  
Three Component Reaction ◽  
Propargyl Alcohols

A photoinduced sulfonylvinylation of unactivated C(sp3)-H bond through a three-component reaction of propargyl alcohols, potassium metabisulfite and cycloketone oxime esters is developed. This approach enables rapid access to cyanoalkylated vinyl...

The Synthesis and Catalytic Application of a New Class of Imprinted Silica

2003 ◽  
Vol 787 ◽  
Author(s):  
John D. Bass ◽  
Sandra L. Anderson ◽  
Alexander Katz
Keyword(s):  
Rational Design ◽  
Chemical Reactivity ◽  
Phenylboronic Acid ◽  
Coupling Reaction ◽  
Suzuki Coupling ◽  
Outer Sphere ◽  
Suzuki Coupling Reaction ◽  
New Class ◽  
Catalytic Application ◽  
Rate Acceleration

AbstractThe effect of chemical environment surrounding a synthetic heterogeneous catalyst active site is investigated using the hydrophilic imprinting of silica. Two model reaction systems have been used for this study: (i) Knoevenagel condensation of 3-nitrobenzaldehyde and malononitrile and (ii) Suzuki coupling of bromobenzene and phenylboronic acid. Using a catalyst in which isolated imprinted amines are surrounded by an acidic silanol-rich environment led to rate accelerations of over 120-fold relative to catalysts in which the amines are surrounded by a hydrophobic environment consisting of trimethylsilyl functional groups for system (i). This result parallels our previous study on the effect of the outer sphere composition on rate acceleration of Knoevenagel reactions using isophthalaldehyde as the aldehyde reactant. We also extended our method for the hydrophilic imprinting of bulk silica to organometallic systems, by successfully synthesizing a tethered palladium complex within the imprinted pocket. This material was used as an active catalyst for (ii). Our results show that a hydrophobic framework environment results in higher initial turnover frequencies than an acidic silanol-rich framework for the Suzuki coupling reaction of bromobenzene and phenylboronic acid, albeit with a lower overall effect than observed in the Knoevenagel system (i). Altogether, these results demonstrate the control of chemical reactivity via the rational design of the outer sphere using an imprinting approach.

scholarly journals PEG-embedded KBr3: A recyclable catalyst for multicomponent coupling reaction for the efficient synthesis of functionalized piperidines

2011 ◽  
Vol 7 ◽  
pp. 1334-1341 ◽  
Author(s):  
Sanny Verma ◽  
Suman L Jain ◽  
Bir Sain
Keyword(s):  
Coupling Reaction ◽  
Recyclable Catalyst ◽  
Efficient Synthesis ◽  
Molecular Bromine ◽  
Keto Ester ◽  
One Step ◽  
High Yields ◽  
Multicomponent Coupling ◽  
Three Component Coupling

PEG-embedded potassium tribromide ([K+PEG]Br3 −) was found to be an efficient and recyclable catalyst for the synthesis of functionalized piperidines in high yields in a one step, three component coupling between aldehyde, amine and β-keto ester. At the end of the reaction the [K+PEG]Br3 − was readily regenerated from the reaction mixture by treating the residue containing [K+PEG]Br− with molecular bromine.

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