Retro-Claisen benzylation: direct use of benzyl alcohols in Pd-catalyzed couplings with nitriles
Literature Information
Publication Date
2014-09-24
DOI
10.1039/C4CC07001A
Impact Factor
6.222
Authors
Tapan Maji, Kinthada Ramakumar, Jon A. Tunge
View Original
Abstract
A new strategy has been developed for the benzylation of nitriles directly from benzyl alcohols. In this process benzyl alcohols undergo retro-Claisen activation with cyanoacetic esters to generate an active electrophile and a carbanionic nucleophile. In the presence of Pd(0) these intermediates undergo catalytic coupling to generate a new C–C bond, resulting in the formation of phenyl propionitriles.
Related Literature
Enhancement of field electron emission in topological insulator Bi2Se3 by Ni doping
Kushal Mazumder, Alfa Sharma, Yogendra Kumar, Mahendra A. More, Rupesh Devan
2018-06-08
Paper
DOI: 10.1039/C8CP01982G
Enhanced fluorescence of phthalimide compounds induced by the incorporation of electron-donating alicyclic amino groups
Ryoji Orita, Marius Franckevičius, Aurimas Vyšniauskas, Vidmantas Gulbinas, Haruki Sugiyama, Hidehiro Uekusa, Kenta Kanosue, Ryohei Ishige, Shinji Ando
2018-05-14
Paper
DOI: 10.1039/C8CP01999A
Thermodiffusion of repulsive charged nanoparticles – the interplay between single-particle and thermoelectric contributions
M. Kouyaté, G. Demouchy, G. Mériguet, R. Aquino, E. Dubois, S. Nakamae, M. Roger, J. Depeyrot, R. Perzynski
2018-05-23
Paper
DOI: 10.1039/C8CP02558D
Most favorable cumulenic structures in iron-capped linear carbon chains are short singlet odd-carbon dications: a theoretical view
Liang Pu, Zhong Zhang, R. Bruce King, Wesley D. Allen
2018-05-21
Paper
DOI: 10.1039/C7CP08673C
The dependence of the β-to-α phase transition behavior of poly(1,4-butylene adipate) on phase separated morphology in its blends with poly(vinylidene fluoride)
Chunyue Hou, Huihui Li, Xiaoli Sun, Yanfang Wang, Shangtao Chen
2018-06-01
Paper
DOI: 10.1039/C8CP02464B
Model – free approach to quadrupole spin relaxation in solid 209Bi-aryl compounds
Danuta Kruk, Christian Goesweiner, Elzbieta Masiewicz, Evrim Umut, Carina Sampl, Hermann Scharfetter
2018-09-04
Paper
DOI: 10.1039/C8CP03848A
Stability of hydrolytic arsenic species in aqueous solutions: As3+vs. As5+
Giuseppe Cassone, Donatella Chillé, Claudia Foti, Ottavia Giuffré, Rosina Celeste Ponterio, Jiri Sponer, Franz Saija
2018-08-27
Paper
DOI: 10.1039/C8CP04320E
Hydrogen bond network structures of protonated short-chain alcohol clusters
Asuka Fujii, Natsuko Sugawara, Po-Jen Hsu, Takuto Shimamori, Ying-Cheng Li, Toru Hamashima, Jer-Lai Kuo
2018-03-05
Perspective
DOI: 10.1039/C7CP08072G
You might also like
Compound Q&A
Is 2-(2-chloroacetamido)-3-phenylpropanoic acid (CAS: 7765-11-9) safe?
2-(2-Chloroacetamido)-3-phenylpropanoic acid (CAS: 7765-11-9) is generally consi...
7765-11-92-(2-chloroacetamido...
Compound Q&A
Is 2-(Benzyloxy)-5-bromobenzoic acid (CAS: 62176-31-2) safe?
2-(Benzyloxy)-5-bromobenzoic acid can be handled safely if appropriate precautio...
62176-31-22-(Benzyloxy)-5-brom...
Compound Q&A
What is (4-Methyl-1,2,5-oxadiazol-3-yl)methanamine hydrochloride (CAS: 1159825-48-5)?
(4-Methyl-1,2,5-oxadiazol-3-yl)methanamine hydrochloride is a chemical compound ...
1159825-48-5(4-Methyl-1,2,5-oxad...
Compound Q&A
What is 2-(5-Hexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS: 917985-54-7)?
2-(5-Hexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS: 917985-54...
917985-54-72-(5-Hexylthiophen-2...
Compound Q&A
Are there alternatives to 4-(8-Methyl-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepin-5-yl)benzenamine (CAS: 102771-26-6) in synthesis?
While 4-(8-Methyl-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepin-5-yl)benzenamine (CAS:...
102771-26-64-(8-Methyl-9H-1,3-d...
Compound Q&A
What is the market or research trend for tert-butyl 3-hydroxy-4,5,7,8-tetrahydro-2H-pyrazolo[3,4-d]azepine-6-carboxylate (CAS: 851376-80-2)?
The market for tert-butyl 3-hydroxy-4,5,7,8-tetrahydro-2H-pyrazolo[3,4-d]azepine...
851376-80-2tert-butyl 3-hydroxy...
Compound Q&A
How should waste containing 3,5-Diamino-1H-pyrazole-4-carbonitrile (CAS: 6844-58-2) be handled?
Waste containing 3,5-Diamino-1H-pyrazole-4-carbonitrile (CAS: 6844-58-2) should ...
6844-58-23,5-Diamino-1H-pyraz...
Compound Q&A
How is (6-Fluoro-3-pyridinyl)boronic acid (CAS: 351019-18-6) typically synthesized?
(6-Fluoro-3-pyridinyl)boronic acid can be synthesized through the reaction of 6-...
351019-18-6(6-Fluoro-3-pyridiny...
Compound Q&A
What industries use Dibenzyl carbonimidoylbiscarbamate (CAS: 10065-79-9)?
Dibenzyl carbonimidoylbiscarbamate (CAS: 10065-79-9) finds applications in vario...
10065-79-9Dibenzyl carbonimido...
Compound Q&A
What is the market or research trend for (beta,beta,2,3,4,5,6-~2~H_7_)Phenylalanine (CAS: 74228-83-4)?
The market for (beta,beta,2,3,4,5,6-~2~H_7_)Phenylalanine (CAS: 74228-83-4) is g...
74228-83-4(beta,beta,2,3,4,5,6...
Source Journal
Chemical Communications
CiteScore:
8.6
Self-citation Rate:
4.7%
Articles per Year:
2458
ChemComm publishes urgent research which is of outstanding significance and interest to experts in the field, while also appealing to the journal’s broad chemistry readership. Our communication format is ideally suited to short, urgent studies that are of such importance that they require accelerated publication. Our scope covers all topics in chemistry, and research at the interface of chemistry and other disciplines (such as materials science, nanoscience, physics, engineering and biology) where there is a significant novelty in the chemistry aspects. Major topic areas covered include: Analytical Chemistry Catalysis Chemical Biology and medicinal chemistry Computational Chemistry and Machine Learning Energy and sustainable chemistry Environmental Chemistry Green Chemistry Inorganic Chemistry Materials Chemistry Nanoscience Organic Chemistry Physical Chemistry Polymer Chemistry Supramolecular Chemistry
Recommended Compounds
2-Methyl 1-(2-methyl-2-propanyl) (2S)-3,3-dimethyl-4-oxo-1,2-pyrrolidinedicarboxylate
CAS Number:
478698-30-5
Molecular Formula:
C13H21NO5
Recommended Suppliers
Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.