Formation of ArF from LPdAr(F): Catalytic Conversion of Aryl Triflates to Aryl Fluorides
Despite increasing pharmaceutical importance, fluorinated aromatic organic molecules remain difficult to synthesize. Present methods require either harsh reaction conditions or highly specialized reagents, making the preparation of complex fluoroarenes challenging. Thus, the development of general m...
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| Format: | Article |
| Language: | en_US |
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American Association for the Advancement of Science (AAAS)
2013
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| Online Access: | http://hdl.handle.net/1721.1/82103 https://orcid.org/0000-0003-3875-4775 |
| _version_ | 1826217316427235328 |
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| author | Watson, Donald A. Su, Mingjuan Teverovskiy, Georgiy Zhang, Yong Garcia-Fortanet, Jorge Kinzel, Tom Buchwald, Stephen Leffler |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Watson, Donald A. Su, Mingjuan Teverovskiy, Georgiy Zhang, Yong Garcia-Fortanet, Jorge Kinzel, Tom Buchwald, Stephen Leffler |
| author_sort | Watson, Donald A. |
| collection | MIT |
| description | Despite increasing pharmaceutical importance, fluorinated aromatic organic molecules remain difficult to synthesize. Present methods require either harsh reaction conditions or highly specialized reagents, making the preparation of complex fluoroarenes challenging. Thus, the development of general methods for their preparation that overcome the limitations of those techniques currently in use is of great interest. We have prepared [LPd(II)Ar(F)] complexes, where L is a biaryl monophosphine ligand and Ar is an aryl group, and identified conditions under which reductive elimination occurs to form an Ar-F bond. On the basis of these results, we have developed a catalytic process that converts aryl bromides and aryl triflates into the corresponding fluorinated arenes by using simple fluoride salts. We expect this method to allow the introduction of fluorine atoms into advanced, highly functionalized intermediates. |
| first_indexed | 2024-09-23T17:01:42Z |
| format | Article |
| id | mit-1721.1/82103 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T17:01:42Z |
| publishDate | 2013 |
| publisher | American Association for the Advancement of Science (AAAS) |
| record_format | dspace |
| spelling | mit-1721.1/821032022-10-03T09:52:49Z Formation of ArF from LPdAr(F): Catalytic Conversion of Aryl Triflates to Aryl Fluorides Watson, Donald A. Su, Mingjuan Teverovskiy, Georgiy Zhang, Yong Garcia-Fortanet, Jorge Kinzel, Tom Buchwald, Stephen Leffler Massachusetts Institute of Technology. Department of Chemistry Watson, Donald A. Su, Mingjuan Teverovskiy, Georgiy Zhang, Yong Garcia-Fortanet, Jorge Kinzel, Tom Buchwald, Stephen Leffler Despite increasing pharmaceutical importance, fluorinated aromatic organic molecules remain difficult to synthesize. Present methods require either harsh reaction conditions or highly specialized reagents, making the preparation of complex fluoroarenes challenging. Thus, the development of general methods for their preparation that overcome the limitations of those techniques currently in use is of great interest. We have prepared [LPd(II)Ar(F)] complexes, where L is a biaryl monophosphine ligand and Ar is an aryl group, and identified conditions under which reductive elimination occurs to form an Ar-F bond. On the basis of these results, we have developed a catalytic process that converts aryl bromides and aryl triflates into the corresponding fluorinated arenes by using simple fluoride salts. We expect this method to allow the introduction of fluorine atoms into advanced, highly functionalized intermediates. National Institutes of Health (U.S.) (Grant GM46059) Merck & Co., Inc. Boehringer Ingelheim Pharmaceuticals BASF National Science Foundation (U.S.) (Grant CHE 9808061) National Institutes of Health (U.S.) (Grant DBI 9729592) 2013-11-13T16:08:39Z 2013-11-13T16:08:39Z 2009-08 2009-06 Article http://purl.org/eprint/type/JournalArticle 0036-8075 1095-9203 http://hdl.handle.net/1721.1/82103 Watson, D. A., M. Su, G. Teverovskiy, Y. Zhang, J. Garcia-Fortanet, T. Kinzel, and S. L. Buchwald. “Formation of ArF from LPdAr(F): Catalytic Conversion of Aryl Triflates to Aryl Fluorides.” Science 325, no. 5948 (September 24, 2009): 1661-1664. https://orcid.org/0000-0003-3875-4775 en_US http://dx.doi.org/10.1126/science.1178239 Science 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 American Association for the Advancement of Science (AAAS) PMC |
| spellingShingle | Watson, Donald A. Su, Mingjuan Teverovskiy, Georgiy Zhang, Yong Garcia-Fortanet, Jorge Kinzel, Tom Buchwald, Stephen Leffler Formation of ArF from LPdAr(F): Catalytic Conversion of Aryl Triflates to Aryl Fluorides |
| title | Formation of ArF from LPdAr(F): Catalytic Conversion of Aryl Triflates to Aryl Fluorides |
| title_full | Formation of ArF from LPdAr(F): Catalytic Conversion of Aryl Triflates to Aryl Fluorides |
| title_fullStr | Formation of ArF from LPdAr(F): Catalytic Conversion of Aryl Triflates to Aryl Fluorides |
| title_full_unstemmed | Formation of ArF from LPdAr(F): Catalytic Conversion of Aryl Triflates to Aryl Fluorides |
| title_short | Formation of ArF from LPdAr(F): Catalytic Conversion of Aryl Triflates to Aryl Fluorides |
| title_sort | formation of arf from lpdar f catalytic conversion of aryl triflates to aryl fluorides |
| url | http://hdl.handle.net/1721.1/82103 https://orcid.org/0000-0003-3875-4775 |
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