Direct Cyclopalladation of Fluorinated Benzyl Amines by Pd3(OAc)6: The Coexistence of Multinuclear Pdn Reaction Pathways Highlights the Importance of Pd Speciation in C–H Bond Activation

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11320%2F23%3A10475813" target="_blank" >RIV/00216208:11320/23:10475813 - isvavai.cz</a>
Alternative codes found
RIV/00216275:25310/23:39920567
Result on the web
<a href="https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=kv5SHPep3C" target="_blank" >https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=kv5SHPep3C</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acs.organomet.3c00178" target="_blank" >10.1021/acs.organomet.3c00178</a>

Result language
angličtina
Original language name
Direct Cyclopalladation of Fluorinated Benzyl Amines by Pd3(OAc)6: The Coexistence of Multinuclear Pdn Reaction Pathways Highlights the Importance of Pd Speciation in C–H Bond Activation
Original language description
Palladacycles are key intermediates in catalytic C-H bond functionalization reactions and important precatalysts for cross-couplings.It is commonly believed that palladacycle formation occurs throughthe reaction of a substrate bearing a C-H bond ortho to a suitable metal-directing group for interaction with, typically,mononuclear "Pd(OAc)(2)" species, with cyclopalladationliberating acetic acid as the side product. In this study, we showthat N,N-dimethyl-fluoro-benzylamines, which can be cyclopalladated either ortho or para to fluorine affording two regioisomericproducts, can occur by a direct reaction of Pd3(OAc)(6), proceeding via higher-order cyclopalladated intermediates.Regioselectivity is altered subtly depending on the ratio of substrate:Pd3(OAc)(6) and the solvent used. Our findings are importantwhen considering mechanisms of Pd-mediated reactions involving theintermediacy of palladacycles, of particular relevance in catalyticC-H bond functionalization chemistry.
Czech name
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Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10301 - Atomic, molecular and chemical physics (physics of atoms and molecules including collision, interaction with radiation, magnetic resonances, Mössbauer effect)

Project
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Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year
2023
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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