Biodegradable, reyclable aprotic Brønsted acids

We are interested (in conjunction with Dr. Nick Gathergood, DCU) in the design of ‘greener’ catalysts. One example is the development of a class of ionic liquids, which are capable of acting as strong acid catalysts, but only in the presence of a protic additive. These materials – which are designed to be biodegradable – are acidic in an ‘on-off’ fashion, and can be safely stored as inert solids until required.


'An organocatalytic process for the hydrolytic cleavage of dithianes mediated by imidazolium ions: no harsh agents required'

L. Myles, N. Gathergood* and S. J. Connon*, Eur. J. Org. Chem., 2015, 188.

LINK

Pub79

'Low antimicrobial toxicity ionic liquids: solvents for asymmetric carbonyl- ene reactions of phenylglyoxal'

R. G. Gore, T. -K. -T. Truong, M. Spulak, S. J. Connon* and N. Gathergood*, Curr. Green Chem. 2014, 1, 239.

LINK

Pub78

'A new generation of aprotic yet Brønsted acidic imidazolium salts: effect of ester/amide groups in the C-2, C-4 and C-5 on antimicrobial toxicity and biodegradation'

R. G. Gore, L. Myles, M. Spulak, I. Beadham, M. T. Garcia, S. J. Connon* and N. Gathergood*, Green Chem201315, 2747.

These 3 Green Chemistry papers were published back to back, also featured on the cover.

LINK

Pub75

'A new generation of aprotic yet Brønsted acidic imidazolium salts: low toxicity, high recyclability and greatly improved activity'

L. Myles, R. G. Gore, N. Gathergood* and S. J. Connon*, Green Chem201315, 2740.

LINK

Pub74

'Tandem ionic liquid antimicrobial toxicity and asymmetric catalysis study: carbonyl-ene reactions with trifluoropyruvate'

R. G. Gore, T. -K. -T. Truong, M. Pour, L. Myles, S. J. Connon* and N. Gathergood*, Green Chem. 201315, 2727.

LINK

Pub73

'The catalytic versatility of non-toxic 1,4-dialkyltriazolium salts:  in situ modification facilitates diametrically opposed catalysis modes in one pot'

L. Myles, N. Gathergood* and S. J. Connon*, Chem. Commun2013, 49, 5316.

LINK

Pub67

'Highly recyclable, imidazolium derived ionic liquids of low antimicrobial and antifungal toxicity: A new strategy for acid catalysis'

L. Myles, R. Gore, Marcel Špulák, N. Gathergood* and S. J. Connon*, Green Chem. 2010, 12, 1157.

LINK

Pub47

'Pyridinium ion catalysis of carbonyl protection reactions'

B. Procuranti, L. Myles, N. Gathergood and S. J. Connon*, Synthesis 2009, 4082.

LINK

Pub43

'Unexpected catalysis: aprotic pyridinium ions as active and recyclable Brønsted acid catalysts in protic media'

B. Procuranti and S. J. Connon*, Org. Lett. 2008, 10, 4935.

Highlighted in Synfacts (2008, 1332)

LINK

Pub38