Synthesis 2011(8): 1157-1192  
DOI: 10.1055/s-0030-1259979
REVIEW
© Georg Thieme Verlag Stuttgart ˙ New York

Lesser-Known Enabling Technologies for Organic Synthesis

Matthew O’Briena, Ross Dentonb, Steven V. Ley*a
a Whiffen Laboratory, Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK
e-Mail: svl1000@cam.ac.uk;
b School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, UK
Further Information

Publication History

Received 24 September 2010
Publication Date:
30 March 2011 (online)

Abstract

In this review we summarize both new emerging technologies as well as some overlooked methods which are beneficial to organic synthesis chemists.

1 Introduction

2 Separation Methods

2.1 Low-Temperature Chromatography

2.2 Reflux Chromatography

2.3 Phase-Switching Methods

2.3.1 Affinity-Based Phase-Switching

2.3.1.1 Fluorous Tags

2.3.1.2 Acid-Base and Polarity Tags

2.3.1.3 Transition-Metal and Ligand Affinity Tags

2.3.1.4 Hydrogen-Bonding Interactions

2.3.1.5 Polyaromatic Affinity Tags

2.3.1.6 Crown Ether Tags

2.3.1.7 Redox-Switchable Tags

2.3.2 Reactive and Irreversible Tags

2.3.2.1 ‘Click’ Tags

2.3.2.2 Diels-Alder Tags

2.3.3 Phase-Switching Involving Precipitation

2.3.3.1 Precipitation by Polymerisation

2.3.3.2 Solubility-Switching

2.3.3.3 Temperature-Dependent Solubility

2.3.4 Size-Exclusion Tags

3 Synthesis Methods

3.1 Cooled Microwave Heating

3.2 Ball-Milling

3.3 Design of Experiments and Related Techniques

4 Conclusion

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