Lithium Diisopropylamide-Mediated Ortholithiation of 2‑Fluoropyridines: Rates, Mechanisms, and the Role of Autocatalysis
Lithium diisopropylamide (LDA)-mediated ortholithiations of 2-fluoropyridine and 2,6-difluoropyridine in tetrahydrofuran at −78 °C were studied using a combination of IR and NMR spectroscopic and computational methods. Rate studies show that a substrate-assisted deaggregation of LDA dimer occurs par...
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| Published in: | Journal of organic chemistry Vol. 78; no. 9; pp. 4214 - 4230 |
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| Main Authors: | , , , , , |
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| Abstract | Lithium diisopropylamide (LDA)-mediated ortholithiations of 2-fluoropyridine and 2,6-difluoropyridine in tetrahydrofuran at −78 °C were studied using a combination of IR and NMR spectroscopic and computational methods. Rate studies show that a substrate-assisted deaggregation of LDA dimer occurs parallel to an unprecedented tetramer-based pathway. Standard and competitive isotope effects confirm post-rate-limiting proton transfer. Autocatalysis stems from ArLi-catalyzed deaggregation of LDA proceeding via 2:2 LDA–ArLi mixed tetramers. A hypersensitivity of the ortholithiation rates to traces of LiCl derives from LiCl-catalyzed LDA dimer–monomer exchange and a subsequent monomer-based ortholithiation. Fleeting 2:2 LDA–LiCl mixed tetramers are suggested to be key intermediates. The mechanisms of both the uncatalyzed and catalyzed deaggregations are discussed. A general mechanistic paradigm is delineated to explain a number of seemingly disparate LDA-mediated reactions, all of which occur in tetrahydrofuran at −78 °C. |
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| AbstractList | Lithium diisopropylamide (LDA)-mediated ortholithiations of 2–fluoropyridine and 2,6–difluoropyridine in tetrahydrofuran at −78 °C were studied using a combination of IR and NMR spectroscopic and computational methods. Rate studies show that a substrate-assisted deaggregation of LDA dimer occurs parallel to an unprecedented tetramer-based pathway. Standard and competitive isotope effects confirm post-rate-limiting proton transfer. Autocatalysis stems from ArLicatalyzed deaggregation of LDA proceeding via 2:2 LDA–ArLi mixed tetramers. A hypersensitivity of the ortholithiation rates to traces of LiCl derives from LiClcatalyzed LDA dimer–monomer exchange and a subsequent monomer-based ortholithiation. Fleeting 2:2 LDA–LiCl mixed tetramers are suggested to be key intermediates. The mechanisms of both the uncatalyzed and catalyzed deaggregations are discussed. A general mechanistic paradigm is delineated to explain a number of seemingly disparate LDA-mediated reactions, all of which occur in tetrahydrofuran at −78 °C. Lithium diisopropylamide (LDA)-mediated ortholithiations of 2-fluoropyridine and 2,6-difluoropyridine in tetrahydrofuran at −78 °C were studied using a combination of IR and NMR spectroscopic and computational methods. Rate studies show that a substrate-assisted deaggregation of LDA dimer occurs parallel to an unprecedented tetramer-based pathway. Standard and competitive isotope effects confirm post-rate-limiting proton transfer. Autocatalysis stems from ArLi-catalyzed deaggregation of LDA proceeding via 2:2 LDA–ArLi mixed tetramers. A hypersensitivity of the ortholithiation rates to traces of LiCl derives from LiCl-catalyzed LDA dimer–monomer exchange and a subsequent monomer-based ortholithiation. Fleeting 2:2 LDA–LiCl mixed tetramers are suggested to be key intermediates. The mechanisms of both the uncatalyzed and catalyzed deaggregations are discussed. A general mechanistic paradigm is delineated to explain a number of seemingly disparate LDA-mediated reactions, all of which occur in tetrahydrofuran at −78 °C. Lithium diisopropylamide (LDA)-mediated ortholithiations of 2-fluoropyridine and 2,6-difluoropyridine in tetrahydrofuran at -78 °C were studied using a combination of IR and NMR spectroscopic and computational methods. Rate studies show that a substrate-assisted deaggregation of LDA dimer occurs parallel to an unprecedented tetramer-based pathway. Standard and competitive isotope effects confirm post-rate-limiting proton transfer. Autocatalysis stems from ArLi-catalyzed deaggregation of LDA proceeding via 2:2 LDA-ArLi mixed tetramers. A hypersensitivity of the ortholithiation rates to traces of LiCl derives from LiCl-catalyzed LDA dimer-monomer exchange and a subsequent monomer-based ortholithiation. Fleeting 2:2 LDA-LiCl mixed tetramers are suggested to be key intermediates. The mechanisms of both the uncatalyzed and catalyzed deaggregations are discussed. A general mechanistic paradigm is delineated to explain a number of seemingly disparate LDA-mediated reactions, all of which occur in tetrahydrofuran at -78 °C. |
| Author | Hoepker, Alexander C Ma, Yun Viciu, Mihai S Gupta, Lekha Faggin, Marc F Collum, David B |
| AuthorAffiliation | Cornell University |
| AuthorAffiliation_xml | – name: Cornell University |
| Author_xml | – sequence: 1 givenname: Lekha surname: Gupta fullname: Gupta, Lekha – sequence: 2 givenname: Alexander C surname: Hoepker fullname: Hoepker, Alexander C – sequence: 3 givenname: Yun surname: Ma fullname: Ma, Yun – sequence: 4 givenname: Mihai S surname: Viciu fullname: Viciu, Mihai S – sequence: 5 givenname: Marc F surname: Faggin fullname: Faggin, Marc F – sequence: 6 givenname: David B surname: Collum fullname: Collum, David B email: dbc6@cornell.edu |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/23270408$$D View this record in MEDLINE/PubMed |
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| Snippet | Lithium diisopropylamide (LDA)-mediated ortholithiations of 2-fluoropyridine and 2,6-difluoropyridine in tetrahydrofuran at −78 °C were studied using a... Lithium diisopropylamide (LDA)-mediated ortholithiations of 2-fluoropyridine and 2,6-difluoropyridine in tetrahydrofuran at -78 °C were studied using a... Lithium diisopropylamide (LDA)-mediated ortholithiations of 2–fluoropyridine and 2,6–difluoropyridine in tetrahydrofuran at −78 °C were studied using a... |
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| SubjectTerms | Catalysis Kinetics Lithium - chemistry Lithium Chloride - chemistry Magnetic Resonance Spectroscopy Molecular Structure Organometallic Compounds - chemistry Propylamines - chemistry Pyridines - chemistry |
| Title | Lithium Diisopropylamide-Mediated Ortholithiation of 2‑Fluoropyridines: Rates, Mechanisms, and the Role of Autocatalysis |
| URI | http://dx.doi.org/10.1021/jo302408r https://www.ncbi.nlm.nih.gov/pubmed/23270408 https://search.proquest.com/docview/1348503649 https://pubmed.ncbi.nlm.nih.gov/PMC3644364 |
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