Concerted nucleophilic aromatic substitutions
Nucleophilic aromatic substitution (S N Ar) is one of the most widely applied reaction classes in pharmaceutical and chemical research, providing a broadly useful platform for the modification of aromatic ring scaffolds. The generally accepted mechanism for S N Ar reactions involves a two-step addit...
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| Published in | Nature chemistry Vol. 10; no. 9; pp. 917 - 923 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
London
Nature Publishing Group UK
01.09.2018
Nature Publishing Group |
| Subjects | |
| Online Access | Get full text |
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| Abstract | Nucleophilic aromatic substitution (S
N
Ar) is one of the most widely applied reaction classes in pharmaceutical and chemical research, providing a broadly useful platform for the modification of aromatic ring scaffolds. The generally accepted mechanism for S
N
Ar reactions involves a two-step addition–elimination sequence via a discrete, non-aromatic Meisenheimer complex. Here we use
12
C/
13
C kinetic isotope effect (KIE) studies and computational analyses to provide evidence that prototypical S
N
Ar reactions in fact proceed through concerted mechanisms. The KIE measurements were made possible by a new technique that leverages the high sensitivity of
19
F as an NMR nucleus to quantitate the degree of isotopic fractionation. This sensitive technique permits the measurement of KIEs on 10 mg of natural abundance material in one overnight acquisition. As a result, it provides a practical tool for performing detailed mechanistic analyses of reactions that form or break C–F bonds.
Nucleophilic aromatic substitution reactions have long been thought to occur primarily via stepwise mechanisms. New and sensitive methodology for measuring carbon kinetic isotope effects now shows that most such substitutions actually occur through concerted mechanisms. |
|---|---|
| AbstractList | Nucleophilic aromatic substitution (S
N
Ar) is one of the most widely applied reaction classes in pharmaceutical and chemical research, providing a broadly useful platform for the modification of aromatic ring scaffolds. The generally accepted mechanism for S
N
Ar reactions involves a two-step addition–elimination sequence via a discrete, non-aromatic Meisenheimer complex. Here we use
12
C/
13
C kinetic isotope effect (KIE) studies and computational analyses to provide evidence that prototypical S
N
Ar reactions in fact proceed through concerted mechanisms. The KIE measurements were made possible by a new technique that leverages the high sensitivity of
19
F as an NMR nucleus to quantitate the degree of isotopic fractionation. This sensitive technique permits the measurement of KIEs on 10 mg of natural abundance material in one overnight acquisition. As a result, it provides a practical tool for performing detailed mechanistic analyses of reactions that form or break C–F bonds.
Nucleophilic aromatic substitution reactions have long been thought to occur primarily via stepwise mechanisms. New and sensitive methodology for measuring carbon kinetic isotope effects now shows that most such substitutions actually occur through concerted mechanisms. Nucleophilic aromatic substitution (SNAr) is one of the most widely applied reaction classes in pharmaceutical and chemical research, providing a broadly useful platform for the modification of aromatic ring scaffolds. The generally accepted mechanism for SNAr reactions involves a two-step addition–elimination sequence via a discrete, non-aromatic Meisenheimer complex. Here we use 12C/13C kinetic isotope effect (KIE) studies and computational analyses to provide evidence that prototypical SNAr reactions in fact proceed through concerted mechanisms. The KIE measurements were made possible by a new technique that leverages the high sensitivity of 19F as an NMR nucleus to quantitate the degree of isotopic fractionation. This sensitive technique permits the measurement of KIEs on 10 mg of natural abundance material in one overnight acquisition. As a result, it provides a practical tool for performing detailed mechanistic analyses of reactions that form or break C–F bonds.Nucleophilic aromatic substitution reactions have long been thought to occur primarily via stepwise mechanisms. New and sensitive methodology for measuring carbon kinetic isotope effects now shows that most such substitutions actually occur through concerted mechanisms. Nucleophilic aromatic substitution (S N Ar) is one of the most widely applied reaction classes in pharmaceutical and chemical research, providing a broadly useful platform for the modification of aromatic ring scaffolds. The generally accepted mechanism for S N Ar reactions involves a two-step addition–elimination sequence via a discrete, non-aromatic Meisenheimer complex. Here we use 12 C/ 13 C kinetic isotope effect (KIE) studies and computational analyses to provide evidence that prototypical S N Ar reactions in fact proceed through concerted mechanisms. The KIE measurements were made possible by a new technique that leverages the high sensitivity of 19 F as an NMR nucleus to quantitate the degree of isotopic fractionation. This sensitive technique permits the measurement of KIEs on 10 mg of natural abundance material in one overnight acquisition. As a result, it provides a practical tool for performing detailed mechanistic analyses of reactions that form or break C–F bonds. Nucleophilic aromatic substitution (SNAr) is one of the most widely applied reaction classes in pharmaceutical and chemical research, providing a broadly useful platform for the modification of aromatic ring scaffolds. The generally accepted mechanism for SNAr reactions involves a two-step addition-elimination sequence via a discrete, non-aromatic Meisenheimer complex. Here we use 12C/13C kinetic isotope effect (KIE) studies and computational analyses to provide evidence that prototypical SNAr reactions in fact proceed through concerted mechanisms. The KIE measurements were made possible by a new technique that leverages the high sensitivity of 19F as an NMR nucleus to quantitate the degree of isotopic fractionation. This sensitive technique permits the measurement of KIEs on 10 mg of natural abundance material in one overnight acquisition. As a result, it provides a practical tool for performing detailed mechanistic analyses of reactions that form or break C-F bonds. Nucleophilic aromatic substitution (S Ar) is one of the most widely applied reaction classes in pharmaceutical and chemical research, providing a broadly useful platform for the modification of aromatic ring scaffolds. The generally accepted mechanism for S Ar reactions involves a two-step addition-elimination sequence via a discrete, non-aromatic Meisenheimer complex. Here we use C/ C kinetic isotope effect (KIE) studies and computational analyses to provide evidence that prototypical S Ar reactions in fact proceed through concerted mechanisms. The KIE measurements were made possible by a new technique that leverages the high sensitivity of F as an NMR nucleus to quantitate the degree of isotopic fractionation. This sensitive technique permits the measurement of KIEs on 10 mg of natural abundance material in one overnight acquisition. As a result, it provides a practical tool for performing detailed mechanistic analyses of reactions that form or break C-F bonds. |
| Author | Besser, Harrison A. Kwan, Eugene E. Jacobsen, Eric N. Zeng, Yuwen |
| Author_xml | – sequence: 1 givenname: Eugene E. orcidid: 0000-0001-7037-0531 surname: Kwan fullname: Kwan, Eugene E. organization: Department of Chemistry & Chemical Biology, Harvard University – sequence: 2 givenname: Yuwen surname: Zeng fullname: Zeng, Yuwen organization: Department of Chemistry & Chemical Biology, Harvard University – sequence: 3 givenname: Harrison A. surname: Besser fullname: Besser, Harrison A. organization: Department of Chemistry & Chemical Biology, Harvard University – sequence: 4 givenname: Eric N. orcidid: 0000-0001-7952-3661 surname: Jacobsen fullname: Jacobsen, Eric N. email: jacobsen@chemistry.harvard.edu organization: Department of Chemistry & Chemical Biology, Harvard University |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/30013193$$D View this record in MEDLINE/PubMed |
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| Snippet | Nucleophilic aromatic substitution (S
N
Ar) is one of the most widely applied reaction classes in pharmaceutical and chemical research, providing a broadly... Nucleophilic aromatic substitution (S Ar) is one of the most widely applied reaction classes in pharmaceutical and chemical research, providing a broadly... Nucleophilic aromatic substitution (SNAr) is one of the most widely applied reaction classes in pharmaceutical and chemical research, providing a broadly... |
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| SubjectTerms | 639/638/403/934 639/638/563/606 Analytical Chemistry Benzene Derivatives - chemistry Biochemistry Carbon - chemistry Carbon Isotopes - chemistry Chemical research Chemistry Chemistry and Materials Science Chemistry/Food Science Computer applications Fluorine - chemistry Fractionation Inorganic Chemistry Isotope effect Isotope fractionation Isotope Labeling Isotopes Kinetics Magnetic Resonance Spectroscopy NMR Nuclear magnetic resonance Organic Chemistry Physical Chemistry Substitution reactions |
| Title | Concerted nucleophilic aromatic substitutions |
| URI | https://link.springer.com/article/10.1038/s41557-018-0079-7 https://www.ncbi.nlm.nih.gov/pubmed/30013193 https://www.proquest.com/docview/2091217869 https://www.proquest.com/docview/2071563662 https://pubmed.ncbi.nlm.nih.gov/PMC6105541 |
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