Communication
Multistep Synthesis Using Modular Flow Reactors: Bestmann–Ohira Reagent for the Formation of Alkynes and Triazoles†
Ian R. Baxendale Dr.,
Steven V. Ley Prof.,
Andrew C. Mansfield,
Christopher D. Smith Dr.,
Ian R. Baxendale Dr.
ITC, Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW (UK), Fax: (+44) 1223-336-362, http://leyitc.ch.cam.ac.uk/
Search for more papers by this authorSteven V. Ley Prof.
ITC, Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW (UK), Fax: (+44) 1223-336-362, http://leyitc.ch.cam.ac.uk/
Search for more papers by this authorAndrew C. Mansfield
Pfizer Global R&D Research Centre, Ramsgate Rd, Sandwich, Kent CT13 9NJ (UK)
Search for more papers by this authorChristopher D. Smith Dr.
ITC, Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW (UK), Fax: (+44) 1223-336-362, http://leyitc.ch.cam.ac.uk/
Search for more papers by this authorIan R. Baxendale Dr.,
Steven V. Ley Prof.,
Andrew C. Mansfield,
Christopher D. Smith Dr.,
Ian R. Baxendale Dr.
ITC, Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW (UK), Fax: (+44) 1223-336-362, http://leyitc.ch.cam.ac.uk/
Search for more papers by this authorSteven V. Ley Prof.
ITC, Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW (UK), Fax: (+44) 1223-336-362, http://leyitc.ch.cam.ac.uk/
Search for more papers by this authorAndrew C. Mansfield
Pfizer Global R&D Research Centre, Ramsgate Rd, Sandwich, Kent CT13 9NJ (UK)
Search for more papers by this authorChristopher D. Smith Dr.
ITC, Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW (UK), Fax: (+44) 1223-336-362, http://leyitc.ch.cam.ac.uk/
Search for more papers by this author†
We gratefully acknowledge financial support from the EPRSC (to I.R.B.), Syngenta and Chemistry Innovation (to C.D.S.), the BP endowment (to S.V.L.) and Pfizer (to A.C.M.).
Graphical Abstract
Multistep in flow: The Seyferth–Gilbert reagent 1 has been applied in a flow system to rapidly synthesize terminal alkynes. The system has been further applied to synthesize triazole 3 from alcohol 2 in a three-step oxidation/homologation/copper(I)-catalyzed azide–alkyne cycloaddition sequence without isolation of intermediates (see scheme).
Abstract
Multistep in flow: The Seyferth–Gilbert reagent 1 has been applied in a flow system to rapidly synthesize terminal alkynes. The system has been further applied to synthesize triazole 3 from alcohol 2 in a three-step oxidation/homologation/copper(I)-catalyzed azide–alkyne cycloaddition sequence without isolation of intermediates (see scheme).
References
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