Palladium chloride catalyzed photochemical Heck reaction

2013 ◽  
Vol 91 (5) ◽  
pp. 348-351 ◽  
Author(s):  
Suresh B. Waghmode ◽  
Sudhir S. Arbuj ◽  
Bina N. Wani ◽  
C.S. Gopinath
Keyword(s):  
Visible Light ◽  
Heck Reaction ◽  
Palladium Nanoparticles ◽  
Bond Formation ◽  
Aryl Halides ◽  
Palladium Chloride ◽  
Carbon Bond ◽  
Excellent Yield ◽  
Carbon Carbon Bond ◽  
Uv Visible

PdCl2 catalyzed carbon–carbon bond formation (Heck reaction) between substituted aryl halides and olefins was carried out without a ligand, under irradiation with UV–visible light. The results demonstrated that UV–visible light accelerated the rate of the reaction, leading to an excellent yield of corresponding products. The recovered palladium nanoparticles could be thermally recycled several times. PdCl2 gave excellent conversion up to the fifth addition of substrate.

scholarly journals Metal-free visible light photoredox enables generation of carbyne equivalents via phosphonium ylide C–H activation

2019 ◽  
Vol 10 (6) ◽  
pp. 1687-1691 ◽  
Author(s):  
Mrinmoy Das ◽  
Minh Duy Vu ◽  
Qi Zhang ◽  
Xue-Wei Liu
Keyword(s):  
Visible Light ◽  
Bond Formation ◽  
Formation Processes ◽  
New Approach ◽  
Carbon Bond ◽  
Metal Free ◽  
Carbon Carbon Bond ◽  
Carbon Carbon Bonds ◽  
Carbon Bonds ◽  
New Strategy

Phosphonium ylides have shown their synthetic usefulness in important carbon–carbon bond formation processes. Our new strategy employs phosphonium ylides as novel carbyne equivalents and features a new approach for constructing carbon–carbon bonds from alkenes.

Heck-Type Cyclization of Oxime Ethers: Stereoselective Carbon—Carbon Bond Formation with Aryl Halides to Produce Heterocyclic Oximes.

ChemInform ◽  
2007 ◽  
Vol 38 (51) ◽  
Author(s):  
Hiroaki Ohno ◽  
Akimasa Aso ◽  
Yoichi Kadoh ◽  
Nobutaka Fujii ◽  
Tetsuaki Tanaka
Keyword(s):  
Bond Formation ◽  
Aryl Halides ◽  
Carbon Bond ◽  
Carbon Carbon Bond

Heck-Type Cyclization of Oxime Ethers: Stereoselective Carbon–Carbon Bond Formation with Aryl Halides To Produce Heterocyclic Oximes

2007 ◽  
Vol 119 (33) ◽  
pp. 6441-6444 ◽  
Author(s):  
Hiroaki Ohno ◽  
Akimasa Aso ◽  
Yoichi Kadoh ◽  
Nobutaka Fujii ◽  
Tetsuaki Tanaka
Keyword(s):  
Bond Formation ◽  
Aryl Halides ◽  
Carbon Bond ◽  
Carbon Carbon Bond

Studies on intramolecular alkylation. XII. Stereochemical aspects of the preparation of β,γ-unsaturated aldehydes from the [2,3]-sigmatropic rearrangement of ammonium ylides

1980 ◽  
Vol 33 (7) ◽  
pp. 1559 ◽  
Author(s):  
LN Mander ◽  
JV Turner
Keyword(s):  
Bond Formation ◽  
Sigmatropic Rearrangement ◽  
Carbon Bond ◽  
Intramolecular Alkylation ◽  
Unsaturated Aldehydes ◽  
Excellent Yield ◽  
Carbon Carbon Bond ◽  
Diastereomeric Pair

The [2,3]-sigmatropic rearrangement of a series of acetonitrile-derived allylic ammonium ylides [RCH2N+ (C4H8)-CHCN; R = 4'-t- butylcyclohexylidenemethyl (3), 4'-t-butylcyclohex-1-enyl (10), 5'-t- butyl-2'-methylcyclohex-1-enyl (14), 4'-t-butyl-2'-methylcyclohex-1- enyl (20)], followed by acid-catalysed hydrolysis in each case, furnished an excellent yield of a diastereomeric pair of β,γ-olefinic aldehydes [(5)/(6), (12)/(13), (15)/(16) and (21)/(22)]. With cyclohexylidene ylide (4) addition of the carbanion to the more exposed (equatorial vector) face is strongly preferred. In the cyclohexenyl examples there is a clear stereoelectronic requirement in opposition to steric forces which leads mainly to axial carbon-carbon bond formation.

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