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Centre for Sustainable Chemical Processes

Recent papers from CSCP researchers

The Whiting group has reported new asymmetric catalysis methods to carry borylation of imines derived unsaturated aldehydes:
 
A selective transformation of enals into chiral g-amino alcohols,
A. D. J. Calow, A. S. Batsanov, A. Pujol, C. Solé, E. Fernández, A. Whiting,
Org. Lett.201315, 4810-4813, DOI: 10.1021/ol4022029,
 
a paper in the bifunctional catalysis area, looking the effect changing the B-N distance upon catalytic activity:
 
Asymmetric synthesis and application of homologous pyrroline-2-alkylboronic acids: Identification of the B-N distance for eliciting bifunctional catalysis of an asymmetric aldol reaction,
A. S. Batsanov, I. Georgiou, P. R. Girling, L. Pommier, H. C. Shen and A. Whiting, 
Asian J. Org. Chem.2013, DOI: 0.1002/ajoc.201300127,
 
and, an article on direct amide formation applied to trying to make peptide bonds which highlights the challenges and opportunities available for more reactive new catalysts:
 
Direct amidation of amino acids and synthesis of dipeptide using arylboronic acid as catalyst,
S. Liu,  Y. Yang,  X. Liu,  A. S. Batsanov and A. Whiting, 
Eur. J. Org. Chem.2013, 5692-5700,DOI: 10.1002/ejoc.201300560.

“An Introduction to Pyrolysis and Catalytic Pyrolysis: Versatile Techniques for Biomass Conversion”
L. Li, J. S. Rowbotham, H. C. Greenwell, and P. W. Dyer,
in “New and Future Developments in Catalysis: Catalytic Biomass Conversion”; S. L. Suib, Ed.; Elsevier, Amsterdam, 2013pp. 174-208.


"Catalytic Decarboxylative Fluorination for the Synthesis of Tri- and Difluoromethyl Arenes."
S. Mizuta, I, Stenhagen, M. O'Duill, J. Wolstenhulme, A. Kirjavainen, S. Forsback, M. Tredwell, G. Sandford, P. Moore, M. Huiban, S. Luthra, J. Passchier, O. Solin, V. Gouverneur,
Org. Lett.201315, 2648-2651. 

 

"Synthesis and molecular structure of a perfluorinated pyridyl carbanion."
N.Colgin, N.J.Tatum,E. Pohl, S.L. Cobb, G. Sandford,
J. Fluorine Chem2012133, 33-37.

 

"Sequential Continuous Flow Processes for the Oxidation of Amines and Azides by using HOF.MeCN",
Christopher B. McPake, Christopher B. Murray and Graham Sandford
ChemSusChem20125, 312-319.

 

 

February 2012Dalton Transactions HOT ArticleThe role of the activator in olefin dimerization catalysis

Despite the fact that the catalytic activity of Cr and W imido complexes in ethylene dimerization processes has been studied by various authors, to date the analogous Mo catalysts have not been studied. In this HOT article, Phil Dyer and co-workers set out to fill this gap in our knowledge and several molybdenum bis(imido) complexes were tested for ethylene dimerization catalysis in combination with EtAlCl2, showing moderate activity when bulky aryl substituents at the imido ligand are employed. In contrast, when MeAlCl2 is used the activity of the catalyst decreases considerably. To understand the role of the activator in these processes the authors have determined the molecular structures of several complexes derived of the reaction of bis(imido) molybdenum compounds with different aluminium halide reagents.

 

"Application of molybdenum bis(imido) complexes in ethylene dimerisation catalysis",
William R. H. Wright, Andrei S. Batsanov, Antonis M. Messinis, Judith A. K. Howard, Robert P. Tooze, Martin J. Hanton and Philip W. Dyer,
Dalton Trans.201241, 5502-11

 


We now think we know how direct amide formation works, a reaction which has been around since 1885 and may have been an important reaction for the origin of life on earth. It likely involves acid activation by H-bonded acid dimers, see Prof. Andy Whiting's paper:


"The Direct Amide Formation Reaction: Mechanism Studies and the Key Role of Carboxylic Acid H-Bonding"
Hayley Charville, D. Jackson, G. Hodges, Andy Whiting and Mark R. Wilson,
Eur. J. Org. Chem.2011, 5981-5990.


Prof. Andy Whiting has recently published a paper that highlights catalytic asymmetric borylation/reduction/oxidation to access amino alcohols with collaborators inSpain:


"Catalytic 1,3-Difunctionalization of Organic Backbones via a Highly Stereoselective, One-pot, Boron Conjugate-Addition/Reduction/Oxidation Process",
C. Solé, A. Tatla, J. Mata, A. Whiting, H. Gulyás and E. Fernandez,
Chem. Eur. J.201117, 14248-14257.

 

"pKa Values of Chiral Bronsted Acid Catalysts: Phosphoric Acids/Amides, Sulfonyl/Sulfuryl Imides, and Perfluorinated TADDOLs (TEFDDOLs)",
P. Christ, A. G. Lindsay, S. S. Vormittag, J-M. Neudçrfl, A. Berkessel and A. C. O' Donoghue,
Chem. Eur. J.201117, 8524.

 

"pKas of the Conjugate Acids of N-heterocyclic Carbenes in Water",
E. M. Higgins, J. A. Sherwood, A. G. Lindsay, J. Armstrong, R. S. Massey, R. W. Alder and A. C. O'Donoghue,
Chem. Commun.201147, 1559.