Dichotomous mechanistic behavior in Narasaka-Heck cyclizations: electron rich Pd-catalysts generate iminyl radicals
Pd-catalyzed cyclizations of oxime esters with pendant alkenes are subject to an unusual ligand controlled mechanistic divergence. Pd-systems modified with electron deficient phosphines ( e.g. P(3,5-(CF 3 ) 2 C 6 H 3 ) 3 ) promote efficient aza-Heck cyclization, wherein C-N bond formation occurs via...
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| Published in | Chemical science (Cambridge) Vol. 7; no. 2; pp. 158 - 1513 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
CAMBRIDGE
Royal Soc Chemistry
01.01.2016
Royal Society of Chemistry |
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| Abstract | Pd-catalyzed cyclizations of oxime esters with pendant alkenes are subject to an unusual ligand controlled mechanistic divergence. Pd-systems modified with electron deficient phosphines (
e.g.
P(3,5-(CF
3
)
2
C
6
H
3
)
3
) promote efficient aza-Heck cyclization, wherein C-N bond formation occurs
via
alkene imino-palladation. Conversely, electron rich ligands, such as P(
t
-Bu)
3
, cause deviation to a SET pathway and, in these cases, C-N bond formation occurs
via
cyclization of an iminyl radical. A series of mechanistic experiments differentiate the two pathways and the scope of the hybrid organometallic radical cyclization is outlined. This study represents a rare example in Pd-catalysis where selection between dichotomous mechanistic manifolds is facilitated solely by choice of phosphine ligand.
Pd-catalyzed cyclizations of oxime esters with pendant alkenes undergo ligand controlled mechanistic divergence. Electron deficient phosphines promote aza-Heck cyclization; electron rich systems favour a SET pathway. Mechanistic experiments differentiate the two manifolds. |
|---|---|
| AbstractList | Pd-catalyzed cyclizations of oxime esters with pendant alkenes are subject to an unusual ligand controlled mechanistic divergence. Pd-systems modified with electron deficient phosphines (
e.g.
P(3,5-(CF
3
)
2
C
6
H
3
)
3
) promote efficient aza-Heck cyclization, wherein C–N bond formation occurs
via
alkene imino-palladation. Conversely, electron rich ligands, such as P(
t
-Bu)
3
, cause deviation to a SET pathway and, in these cases, C–N bond formation occurs
via
cyclization of an iminyl radical. A series of mechanistic experiments differentiate the two pathways and the scope of the hybrid organometallic radical cyclization is outlined. This study represents a rare example in Pd-catalysis where selection between dichotomous mechanistic manifolds is facilitated solely by choice of phosphine ligand. Pd-catalyzed cyclizations of oxime esters with pendant alkenes are subject to an unusual ligand controlled mechanistic divergence. Pd-systems modified with electron deficient phosphines (e.g. P(3,5-(CF3)2C6H3)3) promote efficient aza-Heck cyclization, wherein C-N bond formation occurs via alkene imino-palladation. Conversely, electron rich ligands, such as P(t-Bu)3, cause deviation to a SET pathway and, in these cases, C-N bond formation occurs via cyclization of an iminyl radical. A series of mechanistic experiments differentiate the two pathways and the scope of the hybrid organometallic radical cyclization is outlined. This study represents a rare example in Pd-catalysis where selection between dichotomous mechanistic manifolds is facilitated solely by choice of phosphine ligand. Pd-catalyzed cyclizations of oxime esters with pendant alkenes are subject to an unusual ligand controlled mechanistic divergence. Pd-systems modified with electron deficient phosphines ( e.g. P(3,5-(CF 3 ) 2 C 6 H 3 ) 3 ) promote efficient aza-Heck cyclization, wherein C-N bond formation occurs via alkene imino-palladation. Conversely, electron rich ligands, such as P( t -Bu) 3 , cause deviation to a SET pathway and, in these cases, C-N bond formation occurs via cyclization of an iminyl radical. A series of mechanistic experiments differentiate the two pathways and the scope of the hybrid organometallic radical cyclization is outlined. This study represents a rare example in Pd-catalysis where selection between dichotomous mechanistic manifolds is facilitated solely by choice of phosphine ligand. Pd-catalyzed cyclizations of oxime esters with pendant alkenes undergo ligand controlled mechanistic divergence. Electron deficient phosphines promote aza-Heck cyclization; electron rich systems favour a SET pathway. Mechanistic experiments differentiate the two manifolds. Pd-catalyzed cyclizations of oxime esters with pendant alkenes are subject to an unusual ligand controlled mechanistic divergence. Pd-systems modified with electron deficient phosphines ( P(3,5-(CF ) C H ) ) promote efficient aza-Heck cyclization, wherein C-N bond formation occurs alkene imino-palladation. Conversely, electron rich ligands, such as P( -Bu) , cause deviation to a SET pathway and, in these cases, C-N bond formation occurs cyclization of an iminyl radical. A series of mechanistic experiments differentiate the two pathways and the scope of the hybrid organometallic radical cyclization is outlined. This study represents a rare example in Pd-catalysis where selection between dichotomous mechanistic manifolds is facilitated solely by choice of phosphine ligand. Pd-catalyzed cyclizations of oxime esters with pendant alkenes undergo ligand controlled mechanistic divergence. Electron deficient phosphines promote aza-Heck cyclization; electron rich systems favour a SET pathway. Mechanistic experiments differentiate the two manifolds. Pd-catalyzed cyclizations of oxime esters with pendant alkenes are subject to an unusual ligand controlled mechanistic divergence. Pd-systems modified with electron deficient phosphines ( e.g. P(3,5-(CF 3 ) 2 C 6 H 3 ) 3 ) promote efficient aza-Heck cyclization, wherein C–N bond formation occurs via alkene imino-palladation. Conversely, electron rich ligands, such as P( t -Bu) 3 , cause deviation to a SET pathway and, in these cases, C–N bond formation occurs via cyclization of an iminyl radical. A series of mechanistic experiments differentiate the two pathways and the scope of the hybrid organometallic radical cyclization is outlined. This study represents a rare example in Pd-catalysis where selection between dichotomous mechanistic manifolds is facilitated solely by choice of phosphine ligand. Pd-catalyzed cyclizations of oxime esters with pendant alkenes are subject to an unusual ligand controlled mechanistic divergence. Pd-systems modified with electron deficient phosphines (e.g. P(3,5-(CF3)2C6H3)3) promote efficient aza-Heck cyclization, wherein C-N bond formation occurs via alkene imino-palladation. Conversely, electron rich ligands, such as P(t-Bu)3, cause deviation to a SET pathway and, in these cases, C-N bond formation occurs via cyclization of an iminyl radical. A series of mechanistic experiments differentiate the two pathways and the scope of the hybrid organometallic radical cyclization is outlined. This study represents a rare example in Pd-catalysis where selection between dichotomous mechanistic manifolds is facilitated solely by choice of phosphine ligand.Pd-catalyzed cyclizations of oxime esters with pendant alkenes are subject to an unusual ligand controlled mechanistic divergence. Pd-systems modified with electron deficient phosphines (e.g. P(3,5-(CF3)2C6H3)3) promote efficient aza-Heck cyclization, wherein C-N bond formation occurs via alkene imino-palladation. Conversely, electron rich ligands, such as P(t-Bu)3, cause deviation to a SET pathway and, in these cases, C-N bond formation occurs via cyclization of an iminyl radical. A series of mechanistic experiments differentiate the two pathways and the scope of the hybrid organometallic radical cyclization is outlined. This study represents a rare example in Pd-catalysis where selection between dichotomous mechanistic manifolds is facilitated solely by choice of phosphine ligand. Pd-catalyzed cyclizations of oxime esters with pendant alkenes are subject to an unusual ligand controlled mechanistic divergence. Pd-systems modified with electron deficient phosphines (e.g. P(3,5-(CF3)(2)C6H3)(3)) promote efficient aza-Heck cyclization, wherein C-N bond formation occurs via alkene imino-palladation. Conversely, electron rich ligands, such as P(t-Bu)(3), cause deviation to a SET pathway and, in these cases, C-N bond formation occurs via cyclization of an iminyl radical. A series of mechanistic experiments differentiate the two pathways and the scope of the hybrid organometallic radical cyclization is outlined. This study represents a rare example in Pd-catalysis where selection between dichotomous mechanistic manifolds is facilitated solely by choice of phosphine ligand. |
| Author | Shaw, Megan H Faulkner, Adele Bower, John F Race, Nicholas J |
| AuthorAffiliation | University of Bristol School of Chemistry |
| AuthorAffiliation_xml | – sequence: 0 name: School of Chemistry – sequence: 0 name: University of Bristol – name: a School of Chemistry , University of Bristol , Bristol , BS8 1TS , UK . Email: john.bower@bris.ac.uk ; Fax: +44 117 925 1295 |
| Author_xml | – sequence: 1 givenname: Nicholas J surname: Race fullname: Race, Nicholas J – sequence: 2 givenname: Adele surname: Faulkner fullname: Faulkner, Adele – sequence: 3 givenname: Megan H surname: Shaw fullname: Shaw, Megan H – sequence: 4 givenname: John F surname: Bower fullname: Bower, John F |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/29899895$$D View this record in MEDLINE/PubMed |
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| Keywords | PALLADIUM AMINATION NITRILES ALKENES SYNTHESIS ALLYLATION C-C DIHYDROPYRROLES OXIME ESTERS DERIVATIVES ACCESS |
| Language | English |
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| Publisher | Royal Soc Chemistry Royal Society of Chemistry |
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| Snippet | Pd-catalyzed cyclizations of oxime esters with pendant alkenes are subject to an unusual ligand controlled mechanistic divergence. Pd-systems modified with... Pd-catalyzed cyclizations of oxime esters with pendant alkenes undergo ligand controlled mechanistic divergence. Electron deficient phosphines promote aza-Heck... |
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| SubjectTerms | Alkenes Bonding Chemistry Chemistry, Multidisciplinary Esters Ligands Palladium Pathways Phosphines Physical Sciences Radicals Science & Technology |
| Title | Dichotomous mechanistic behavior in Narasaka-Heck cyclizations: electron rich Pd-catalysts generate iminyl radicals |
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