Palladium/di-1-adamantyl-n-butylphosphine-catalyzed reductive carbonylation of aryl and vinyl halides

Brennführer, Anne; Neumann, Helfried; Klaus, Stefan; Riermeier, Thomas H.; Almena, Juan; Beller, Matthias

doi:10.1016/j.tet.2007.02.043

Cited by 86 publications

(22 citation statements)

References 70 publications

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“…The Hammett s À parameter [76,77] is an excellent descriptor in this case. Note, however, that the literature contains diverse reports: Similar correlations were reported for Suzuki, [78][79][80] Heck, [81][82][83][84][85] and carbonylation reactions [86] even though different Hammett parameters were used: Milstein and Herrmann reported that s À p parameters yielded the best fits, whereas other studies applied s p parameters. Even a s þ p correlation to establish a stabilization of a positive charge in the transition state was reported.…”

mentioning

confidence: 61%

Insights into Sonogashira Cross‐Coupling by High‐Throughput Kinetics and Descriptor Modeling

Heiden

Plenio

Immel

et al. 2008

Chemistry A European J

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A method is presented for the high-throughput monitoring of reaction kinetics in homogeneous catalysis, running up to 25 coupling reactions in a single reaction vessel. This method is demonstrated and validated on the Sonogashira reaction, analyzing the kinetics for almost 500 coupling reactions. First, one-pot reactions of phenylacetylene with a set of 20 different meta- and para-substituted aryl bromides were analyzed in the presence of 17 different Pd-phosphine complexes. In addition, the temperature-dependent Sonogashira reactions were examined for 21 different ArX (X=Cl, Br, I) substrates, and the corresponding activation enthalpies and entropies were determined by means of Eyring plots: ArI (DeltaH(not equal)=48-62 kJ mol(-1); DeltaS(not equal)=-71--39 J mol(-1) K; NO(2)-->OMe), ArBr (DeltaH(not equal)=54-82 kJ mol(-1), DeltaS(not equal)=-55-11 J mol(-1) K), and ArCl (DeltaH(not equal)=95-144 kJ mol(-1), DeltaS(not equal)=-6-100 J mol(-1) K). DFT calculations established a linear correlation of DeltaH( not equal) and the Kohn-Sham HOMO energies of ArX (X=Cl, Br, I) and confirmed their involvement in the rate-limiting step. However, despite different C--X bond energies, aryl iodides and electron-deficient aryl bromides showed similar activation parameters.

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mentioning

confidence: 61%

Insights into Sonogashira Cross‐Coupling by High‐Throughput Kinetics and Descriptor Modeling

Heiden

Plenio

Immel

et al. 2008

Chemistry A European J

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“…Substituted b-arylvinyl bromides act as extremely versatile precursors for the Pd(0) (1) and Ni(0) (2) mediated syntheses of various diene and eneyne systems, a,b-unsaturated aldehydes (3), and a,bunsaturated carboxylic acids (4) as well as in CuI-Lproline-mediated reactions with active methylene compounds for the synthesis of a-methylene enones (5), Ullmann reaction with imidazole in ionic liquid (6), enantioselective synthesis of (') (S,S)-reboxetine (7), stereoselective synthesis of vinyl selenide using catalytic amount of CuI in [bmIm]BF 4 (8), construction of furan moiety by Suzuki coupling (9), and stereocontrolled synthesis of a,a-difluorosubstituted phenyl butenoate (10). (E)-b-arylvinyl bromides were classically prepared by Hunsdiecker reaction (11Á13).…”

Section: Introductionmentioning

confidence: 99%

Sodium tungstate-catalyzed “On-water” synthesis of β-arylvinyl bromides

Roy¹,

Bhar

2010

Green Chemistry Letters and Reviews

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“…Among the cross‐coupled carbonylative products, aldehydes are considered as important substrates due to their wide applications in organic synthesis, the aldehyde functional group being key intermediates in an array of synthetic reactions. Palladium‐catalysed reductive carbonylation of aryl or vinyl halides to aldehydes is one of the most synthetically used carbonylation reactions . However, only limited procedures have been developed for this synthetically important method.…”

Section: Introductionmentioning

confidence: 99%

Palladium‐catalysed reductive carbonylation of aryl halides with iron pentacarbonyl for synthesis of aromatic aldehydes and deuterated aldehydes

Iranpoor

Firouzabadi

Etemadi‐Davan

et al. 2015

Applied Organom Chemis

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The first use of iron pentacarbonyl is described for the novel and efficient conversion of aryl iodides, bromides and chlorides into their corresponding aryl aldehydes and/or aryl deuterated aldehydes. The reaction is catalysed with Pd(0) in aqueous N,N‐dimethylformamide at atmospheric pressure. In this protocol, neither gaseous hydrogen nor any reducing agent is required for the formation of the carbonylated product. The reaction can be performed without a P(III) ligand for aryl iodides; however, employing a P(III) ligand is necessary to perform the reaction with aryl bromides and chlorides. Copyright © 2015 John Wiley & Sons, Ltd.

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Palladium/di-1-adamantyl-n-butylphosphine-catalyzed reductive carbonylation of aryl and vinyl halides

Cited by 86 publications

References 70 publications

Insights into Sonogashira Cross‐Coupling by High‐Throughput Kinetics and Descriptor Modeling

Insights into Sonogashira Cross‐Coupling by High‐Throughput Kinetics and Descriptor Modeling

Sodium tungstate-catalyzed “On-water” synthesis of β-arylvinyl bromides

Palladium‐catalysed reductive carbonylation of aryl halides with iron pentacarbonyl for synthesis of aromatic aldehydes and deuterated aldehydes

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