Dosage delivery of sensitive reagents enables glove-box-free synthesis.
Contemporary organic chemists employ a broad range of catalytic and stoichiometric methods to construct molecules for applications in the material sciences, and as pharmaceuticals, agrochemicals, and sensors. The utility of a synthetic method may be greatly reduced if it relies on a glove box to enable the use of air- and moisture-sensitive reagents or catalysts. Furthermore, many synthetic chemistry laboratories have numerous containers of partially used reagents that have been spoiled by exposure to the ambient atmosphere. This is exceptionally wasteful from both an environmental and a cost perspective. Here we report an encapsulation method for stabilizing and storing air- and moisture-sensitive compounds. We demonstrate this approach in three contexts, by describing single-use capsules that contain all of the reagents (catalysts, ligands, and bases) necessary for the glove-box-free palladium-catalysed carbon-fluorine, carbon-nitrogen, and carbon-carbon bond-forming reactions. This strategy should reduce the number of error-prone, tedious and time-consuming weighing procedures required for such syntheses and should be applicable to a wide range of reagents, catalysts, and substrate combinations.
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Aaron C
AC
Sather
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Hong Geun
HG
Lee
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
James R
JR
Colombe
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Anni
A
Zhang
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Stephen L
SL
Buchwald
D000588:Amines / Q000737:chemistry; D001965:Bromides / Q000737:chemistry; D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D005461:Fluorine / Q000737:chemistry; D007202:Indicators and Reagents; D008024:Ligands; D009584:Nitrogen / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D014885:Waxes / Q000737:chemistry
D000588:Amines; D001965:Bromides; D007202:Indicators and Reagents; D008024:Ligands; D009942:Organometallic Compounds; D014885:Waxes; D005461:Fluorine; D010165:Palladium; D002244:Carbon; D009584:Nitrogen