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 ena...
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| Format: | Article |
| Language: | en_US |
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Springer Nature
2016
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| Online Access: | http://hdl.handle.net/1721.1/104849 https://orcid.org/0000-0003-3928-2984 https://orcid.org/0000-0001-8075-1100 https://orcid.org/0000-0002-8750-7968 https://orcid.org/0000-0003-3875-4775 |
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| author | Sather, Aaron C. Lee, Hong Geun Colombe, James Robert Zhang, Anni Buchwald, Stephen Leffler |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Sather, Aaron C. Lee, Hong Geun Colombe, James Robert Zhang, Anni Buchwald, Stephen Leffler |
| author_sort | Sather, Aaron C. |
| collection | MIT |
| description | 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. |
| first_indexed | 2024-09-23T17:01:15Z |
| format | Article |
| id | mit-1721.1/104849 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T17:01:15Z |
| publishDate | 2016 |
| publisher | Springer Nature |
| record_format | dspace |
| spelling | mit-1721.1/1048492022-09-29T23:09:15Z Dosage delivery of sensitive reagents enables glove-box-free synthesis Sather, Aaron C. Lee, Hong Geun Colombe, James Robert Zhang, Anni Buchwald, Stephen Leffler Massachusetts Institute of Technology. Department of Chemistry Sather, Aaron C. Lee, Hong Geun Colombe, James Robert Zhang, Anni Buchwald, Stephen Leffler 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. National Science Foundation (U.S.) (Pre-doctoral fellowship (1122374)) National Institutes of Health (U.S.) (Postdoctoral fellowship (1F32GM108092-01A1)) National Institutes of Health (U.S.) (Award number R01GM46059) 2016-10-19T15:34:24Z 2016-10-19T15:34:24Z 2015-08 2015-04 Article http://purl.org/eprint/type/JournalArticle 0028-0836 1476-4687 http://hdl.handle.net/1721.1/104849 Sather, Aaron C., Hong Geun Lee, James R. Colombe, Anni Zhang, and Stephen L. Buchwald. “Dosage Delivery of Sensitive Reagents Enables Glove-Box-Free Synthesis.” Nature 524, no. 7564 (August 12, 2015): 208–211. © 2015 Nature Publishing Group. https://orcid.org/0000-0003-3928-2984 https://orcid.org/0000-0001-8075-1100 https://orcid.org/0000-0002-8750-7968 https://orcid.org/0000-0003-3875-4775 en_US http://dx.doi.org/10.1038/nature14654 Nature Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use. application/pdf Springer Nature PMC |
| spellingShingle | Sather, Aaron C. Lee, Hong Geun Colombe, James Robert Zhang, Anni Buchwald, Stephen Leffler Dosage delivery of sensitive reagents enables glove-box-free synthesis |
| title | Dosage delivery of sensitive reagents enables glove-box-free synthesis |
| title_full | Dosage delivery of sensitive reagents enables glove-box-free synthesis |
| title_fullStr | Dosage delivery of sensitive reagents enables glove-box-free synthesis |
| title_full_unstemmed | Dosage delivery of sensitive reagents enables glove-box-free synthesis |
| title_short | Dosage delivery of sensitive reagents enables glove-box-free synthesis |
| title_sort | dosage delivery of sensitive reagents enables glove box free synthesis |
| url | http://hdl.handle.net/1721.1/104849 https://orcid.org/0000-0003-3928-2984 https://orcid.org/0000-0001-8075-1100 https://orcid.org/0000-0002-8750-7968 https://orcid.org/0000-0003-3875-4775 |
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