Highly Regioselective Catalytic Oxidative Coupling Reactions:  Synthetic and Mechanistic Investigations

Hull, Kami L.; Lanni, Erica L.; Sanford, Melanie S.

doi:10.1021/ja065718e

Cited by 333 publications

(156 citation statements)

References 14 publications

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“…Thus, it is obvious that such weak oxidants as oxygen (−0.78 to −1.26 V), 1,4-benzoquinone (0.16 to −0.875V) are not able to oxidize many palladacycles even up to Pd(III) (~0.25 to 1.4 V) complexes, the more so to Pd(IV) (~1.0 to 1.6V) [25]. This explains the numerous failed attempts to use them in such Pd-catalysed C-H functionalizations, such as 1,4-benzoquinone [27][28][29]75,[82][83][84][85], and O 2 [77,82,[86][87][88] for example.…”

Section: Methodsmentioning

confidence: 99%

Redox-Induced Aromatic C–H Bond Functionalization in Metal Complex Catalysis from the Electrochemical Point of View

2017

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This review generalizes and specifies the oxidizing ability of a number of oxidants used in palladium (Pd)-catalyzed aromatic C-H functionalizations. The redox potentials have been analyzed as the measure of oxidant strength and applied to the reasoning of the efficiency of known reactions where catalytic cycles include cyclometalated palladium complexes (and other organopalladium key intermediates).

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Section: Methodsmentioning

confidence: 99%

Redox-Induced Aromatic C–H Bond Functionalization in Metal Complex Catalysis from the Electrochemical Point of View

2017

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“…A range of different oxidants were examined for the reaction, interestingly, oxidants, for example, air, AgF, and AgOAc, that were effective in previously reported reactions were found to be unsuccessful. [48] Ozone in the presence of palladium(II) acetate (5 mol %) was found to be effective. The reaction was high yielding and regioselective for a range of 2-arylpyridines.…”

Section: Other Metalsmentioning

confidence: 97%

“…[45][46][47] Moreover, a successful and regioselective CDC for the synthesis of biaryls catalyzed by palladium(II) in the presence of the terminal oxidant ozone has been reported. [48] 2-Arylpyridines have been coupled to give the biaryl products in a highly regioselective manner at room temperature with the sole byproduct being two protons. A range of different oxidants were examined for the reaction, interestingly, oxidants, for example, air, AgF, and AgOAc, that were effective in previously reported reactions were found to be unsuccessful.…”

Section: Other Metalsmentioning

confidence: 99%

Beyond Traditional Cross Couplings: The Scope of the Cross Dehydrogenative Coupling Reaction

Scheuermann

2010

Chemistry An Asian Journal

636

104

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Dedicated to the 150th anniversary of Japan-UK diplomatic relations FOCUS REVIEWSAbstract: The development of new and environmentally compatible methods for the synthesis of CÀC and CÀhet-eroatom bonds is of great significance to researchers. The cross dehydrogenative coupling (CDC) is emerging as an important tool for chemists with a variety of, often inexpensive, metal catalysts able to perform these reactions both regio-and enantioselectively. Perhaps more importantly CDC methodology has been shown to be extremely environmentally friendly and facile being able to be carried out in aqueous environments under an atmosphere of air. This Focus Review intends to give an overview of the most contemporary developments in this exciting and emerging area of cross-coupling chemistry.

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“…82 The proposed mechanism is illustrated in Figure 27. The palladation of 55 affords cyclometallated 116.…”

Section: -Carbon-carbon Bond Formation: Arylationsmentioning

confidence: 99%

Orthometallation as a Strategy in Pd-mediated Organic Synthesis

Camaño¹,

Cuesta²,

Nieto³

et al. 2011

COC

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Abstract:The orthopalladated complexes are among the most representative Pd(II) compounds. They display a wide prospect of applications, but they are mainly known by their use as intermediates in metal-mediated organic synthesis. In this review we describe how palladacycles are used to build up new molecules through regioselective formation of C-halogen, C-O, C-N, C-P, C-S and C-C bonds, either under catalytic or stoichiometric conditions. This methodology is based on the selective incorporation of the Pd into the organic skeleton to be modified and subsequent reactivity of the Pd-C bond toward different substrates. In many cases this strategy is alternative or even competitive, improving standard organic methods. The most recent achievements of the last five years will be covered here, presenting only the most impressive results.

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Highly Regioselective Catalytic Oxidative Coupling Reactions: Synthetic and Mechanistic Investigations

Cited by 333 publications

References 14 publications

Redox-Induced Aromatic C–H Bond Functionalization in Metal Complex Catalysis from the Electrochemical Point of View

Redox-Induced Aromatic C–H Bond Functionalization in Metal Complex Catalysis from the Electrochemical Point of View

Beyond Traditional Cross Couplings: The Scope of the Cross Dehydrogenative Coupling Reaction

Orthometallation as a Strategy in Pd-mediated Organic Synthesis

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