Quaternary Ammonium Trifluoromethoxide Salts as Stable Sources of Nucleophilic OCF3
The reaction of nucleophilic tertiary amines with trifluoromethyl and pentafluoroethyl methyl ethers provides quaternary ammonium trifluoromethoxide (NR4OCF3) and pentafluoroethoxide (NR4OCF2CF3) salts, respectively, in good yields. The new trifluoromethoxide salts disclosed herein are uniquely stab...
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| Published in | Organic letters Vol. 22; no. 5; pp. 1785 - 1790 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
06.03.2020
Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
| ISSN | 1523-7060 1523-7052 1523-7052 |
| DOI | 10.1021/acs.orglett.0c00099 |
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| Abstract | The reaction of nucleophilic tertiary amines with trifluoromethyl and pentafluoroethyl methyl ethers provides quaternary ammonium trifluoromethoxide (NR4OCF3) and pentafluoroethoxide (NR4OCF2CF3) salts, respectively, in good yields. The new trifluoromethoxide salts disclosed herein are uniquely stable for extended periods of time in both the solid state and in solution, which complements contemporary reagents. Here we describe the preparation of a range of NR4OCF3 salts, their long-term stability, and utility in substitution reactions. |
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| AbstractList | The reaction of nucleophilic tertiary amines with trifluoromethyl and pentafluoroethyl methyl ethers provides quaternary ammonium trifluoromethoxide (NR4OCF3) and pentafluoroethoxide (NR4OCF2CF3) salts, respectively, in good yields. The new trifluoromethoxide salts disclosed herein are uniquely stable for extended periods of time in both the solid state and in solution, which complements contemporary reagents. Here we describe the preparation of a range of NR4OCF3 salts, their long-term stability, and utility in substitution reactions.The reaction of nucleophilic tertiary amines with trifluoromethyl and pentafluoroethyl methyl ethers provides quaternary ammonium trifluoromethoxide (NR4OCF3) and pentafluoroethoxide (NR4OCF2CF3) salts, respectively, in good yields. The new trifluoromethoxide salts disclosed herein are uniquely stable for extended periods of time in both the solid state and in solution, which complements contemporary reagents. Here we describe the preparation of a range of NR4OCF3 salts, their long-term stability, and utility in substitution reactions. The reaction of nucleophilic tertiary amines with trifluoromethyl and pentafluoroethyl methyl ethers provides quaternary ammonium trifluoromethoxide (NR4OCF3) and pentafluoroethoxide (NR4OCF2CF3) salts, respectively, in good yields. The new trifluoromethoxide salts disclosed herein are uniquely stable for extended periods of time in both the solid state and in solution, which complements contemporary reagents. Here we describe the preparation of a range of NR4OCF3 salts, their long-term stability, and utility in substitution reactions. |
| Author | Martin, Rainer E Meanwell, Michael Newton, Josiah J Britton, Robert Jelier, Benson J Friesen, Chadron M |
| AuthorAffiliation | Department of Chemistry Medicinal Chemistry, Roche Pharma Research and Early Development (pRED), Roche Innovation Center Basel |
| AuthorAffiliation_xml | – name: Medicinal Chemistry, Roche Pharma Research and Early Development (pRED), Roche Innovation Center Basel – name: Department of Chemistry |
| Author_xml | – sequence: 1 givenname: Josiah J surname: Newton fullname: Newton, Josiah J organization: Department of Chemistry – sequence: 2 givenname: Benson J surname: Jelier fullname: Jelier, Benson J organization: Department of Chemistry – sequence: 3 givenname: Michael surname: Meanwell fullname: Meanwell, Michael organization: Department of Chemistry – sequence: 4 givenname: Rainer E orcidid: 0000-0001-7895-497X surname: Martin fullname: Martin, Rainer E organization: Medicinal Chemistry, Roche Pharma Research and Early Development (pRED), Roche Innovation Center Basel – sequence: 5 givenname: Robert orcidid: 0000-0002-9335-0047 surname: Britton fullname: Britton, Robert email: rbritton@sfu.ca organization: Department of Chemistry – sequence: 6 givenname: Chadron M orcidid: 0000-0001-9955-5695 surname: Friesen fullname: Friesen, Chadron M email: chad.friesen@twu.ca organization: Department of Chemistry |
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| Keywords | ALKENES POTENT TETRAMETHYLAMMONIUM TRIFLUOROMETHYLTHIOLATION AMINES DIAZO ESTERS TRIFLUOROMETHYLSELENOLATION ARYL IODIDES |
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publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja210364r |
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| Snippet | The reaction of nucleophilic tertiary amines with trifluoromethyl and pentafluoroethyl methyl ethers provides quaternary ammonium trifluoromethoxide (NR4OCF3)... |
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| SubjectTerms | Chemistry Chemistry, Organic Physical Sciences Science & Technology |
| Title | Quaternary Ammonium Trifluoromethoxide Salts as Stable Sources of Nucleophilic OCF3 |
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