Of the ortho effect in palladium/norbornene-catalyzed reactions: A theoretical investigation

Journal of the American Chemical Society

Volumn 133, Issue 22, 2011, Pages 8574-8585

  Maestri, Giovanni ^a,b   Motti, Elena ^a   Della Ca', Nicola ^a   Malacria, Max ^b   Derat, Etienne ^b   Catellani, Marta ^a  

^a UNIVERSITY OF PARMA   (Italy)

^b Université Pierre et Marie Curie   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL HALIDES; ARYL-ARYL COUPLING; BIPYRAMIDAL STRUCTURES; DFT CALCULATION; ENERGETIC DIFFERENCES; ENERGY TRANSITION STATE; IN-SITU; METALLACYCLES; NORBORNENES; ORTHO EFFECT; OXIDATIVE ADDITIONS; PALLADACYCLES; PALLADIUM-CATALYZED REACTIONS; REDUCTIVE ELIMINATION; STERIC EFFECT; THEORETICAL INVESTIGATIONS; TRANSITION STATE; TRANSMETALATION;

ADDITION REACTIONS; CATALYSIS; METAL HALIDES; PALLADIUM COMPOUNDS;

REACTION INTERMEDIATES;

CARBON; HALIDE; NORBORNENE DERIVATIVE; PALLADIUM;

ADDITION REACTION; ARTICLE; CATALYSIS; DENSITY FUNCTIONAL THEORY; ENERGY; MOLECULE; OXIDATION; REACTION ANALYSIS;

EID: 79958010991     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja110988p     Document Type: Article

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126. TS(V-VI)a could be found employing B3LYP and PBE0 functionals. They lie only +0.3 and +0.8 kcal/mol above VIa, respectively.
127. See Supporting Information Section 2. Single-points calculations on these relevant TSs for reactions a-c favor the TM pathway by 0.5-2 kcal/mol.
128. We modeled also this system, as proposed by Cardenas and Echavarren in their model, but the resulting energies are higher than those reported in Figure 3. This is probably related to the simplified model they employed, where steric congestion was much lower.
129. See Supporting Information Section 2. Single-points calculations on these relevant TSs for reactions d-f favor the TM pathway by 4-8 kcal/mol.
130. Using B3LYP and PBE0 functionals did not allow to determine either the TS or intermediate VIg, and led to a direct connection, although very energetically disfavored, between Vg and TS(VI-VII)g.
131. See Supporting Information Section 2. Single-points calculations on these relevant TSs for reactions g-k favor the Pd(IV) pathway by 8-17 kcal/mol.
132. 2-Substituted aryl halides have been tested as simplified model substrates for catalytic methods featuring a final intramolecular ring closure, as those of refs 17c-17e.
133. The distance, as reported above, is reduced by 0.03 Å only, while this contraction is greater (0.23 Å) when the Me group is replaced by a H atom, as found for Ia and its corresponding TS(II-III)a.
134. The methyl group in our model, or even much more sterically demanding groups such as the i -Pr, s -Bu, and Ph, were experimentally employed in successful way.
135. Modeled relevant structures evidencing these further H-H close proximity (less than 2 Å) for i,k,n and p systems could be found in the Supporting Information.
136. See Supporting Information Section 2. Single-points calculations on these relevant TSs for reactions l-p favor the Pd(IV) pathway by 1-10 kcal.
137. See Supporting Information Section 3. Single-points calculations on these relevant TSs for reactions g-p favor in all cases this reductive elimination pathway by 3-16 kcal/mol.
138. Relevant data for these three reacting carbon atoms and relevant calculated charges for palladium nuclei of both formal Pd(IV) and transmetalation (TM) mechanisms are available in the Section 8 of Supporting Information.