Transition Metal‐Mediated Carbon–Heteroatom Cross‐Coupling (C—N, C—O, C—S, C—Se, C—Te, C—P, C—As, C—Sb, and C—B Bond Forming Reactions)

Kannan, Masanam; Sengoden, Mani; Punniyamurthy, Tharmalingam

doi:10.1002/9781118754887.ch20

Cited by 2 publications

(2 citation statements)

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“…Amide bond formation is a fundamentally important reaction in organic synthesis, and the amide functionality is a common feature in small and complex, synthetic and natural molecules, which widely exist in pharmaceuticals and agrochemicals . The cross-coupling reactions that form C–N bonds have become useful methods to synthesize anilines and amides, which are an important class of compounds throughout chemical research . The applications of Pd-catalyzed C–N cross-coupling reactions in the synthesis of heterocycles and pharmaceuticals, materials science, and natural product synthesis have been reviewed. ,− The prominent examples are the synthesis of the fungicides sedaxane 109 and mepanipyrim 115 and the acaricide bifenazate 52 .…”

Section: Carbon–nitrogen Bond Forming Cross-couplingsmentioning

confidence: 99%

Palladium-Catalyzed Cross-Coupling Reactions: A Powerful Tool for the Synthesis of Agrochemicals

Devendar

Kang

et al. 2018

J. Agric. Food Chem.

328

165

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Pd-catalyzed cross-coupling reactions have become essential tools for the construction of carbon-carbon and carbon-heteroatom bonds. Over the last three decades, great efforts have been made with cross-coupling chemistry in the discovery, development, and commercialization of innovative new pharmaceuticals and agrochemicals (mainly herbicides, fungicides, and insecticides). In view of the growing interest in both modern crop protection and cross-coupling chemistry, this review gives a comprehensive overview of the successful applications of various Pd-catalyzed cross-coupling methodologies, which have been implemented as key steps in the synthesis of agrochemicals (on R&D and pilot-plant scales) such as the Heck, Suzuki, Sonogashira, Stille, and Negishi reactions, as well as decarboxylative, carbonylative, α-arylative, and carbon-nitrogen bond bond-forming cross-coupling reactions. Some perspectives and challenges for these catalytic coupling processes in the discovery of agrochemicals are briefly discussed in the final section. The examples chosen demonstrate that cross-coupling chemistry approaches open-up new, low-cost, and more efficient industrial routes to existing agrochemicals, and such methods also have the capability to lead the new generation of pesticides with novel modes of action for sustainable crop protection.

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Section: Carbon–nitrogen Bond Forming Cross-couplingsmentioning

confidence: 99%

Palladium-Catalyzed Cross-Coupling Reactions: A Powerful Tool for the Synthesis of Agrochemicals

Devendar

Kang

et al. 2018

J. Agric. Food Chem.

328

165

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“…The resultant amination reaction, now known as Buchwald–Hartwig amination, successfully coupled C-sp 2 electrophiles with a range of nitrogen nucleophiles and has become a critical reaction in the development of pharmaceutical agents and other amine containing materials. Over the intervening years, a number of related heteroatomic nucleophiles and ranges of catalysts have also been shown to be compatible with this general process. ,− Mechanistically, studies have shown that these processes are closely related to the more classical C–C bond forming reactions and proceed via initial oxidative addition of the low-valent metal catalyst to the C-sp 2 electrophile, which undergoes exchange of anionic ligands and ultimately reductive elimination provides the observed products (Figure ). , Additionally, during this time, catalytic protocols for cross-coupling aryl halides to heteroatomic nucleophiles based on classical Goldberg reactions were developed , as well as oxidative protocols to cross-couple nucleophilic C-sp 2 nucleophiles (e.g., aryl boronic acids) to heteroatomic nucleophiles. − Not only are all of these protocols important means of accessing heteroatom-containing organic molecules, they also highlight the compatibility of heteroatoms in cross-coupling reactions.…”

Section: Introductionmentioning

confidence: 97%

Cross-Coupling of Heteroatomic Electrophiles

2019

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At the advent of cross-coupling chemistry, carbon electrophiles based on halides or psuedohalides were the only suitable electrophilic coupling partners. Almost two decades passed before the first cross-coupling reaction of heteroatom-based electrophiles was reported. Early work by Murai and Tanaka initiated investigations into silicon electrophiles. Narasaka and Johnson pioneered the way in the use of nitrogen electrophiles; while Suginome began the exploration of boron electrophiles. The chemistry reviewed within provides prospective on the use of heteroatomic electrophiles specifically silicon-, nitrogen-, boron-, oxygen-and phosphorus-based electrophiles in transitionmetal catalyzed cross-coupling. For the purposes of this review, a loose definition of crosscoupling is utilized; all reactions minimally proceed via an oxidative addition event. Although not cross-coupling in a traditional sense, we have also included catalyzed reactions that join a heteroatomic electrophile with an in situ generated nu-cleophile. However, for brevity, those involving hydroamination or C-H activation as a key step are largely excluded. This work includes primary references published up to and including October 2018.

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Transition Metal‐Mediated Carbon–Heteroatom Cross‐Coupling (C—N, C—O, C—S, C—Se, C—Te, C—P, C—As, C—Sb, and C—B Bond Forming Reactions)

Cited by 2 publications

References 312 publications

Palladium-Catalyzed Cross-Coupling Reactions: A Powerful Tool for the Synthesis of Agrochemicals

Palladium-Catalyzed Cross-Coupling Reactions: A Powerful Tool for the Synthesis of Agrochemicals

Cross-Coupling of Heteroatomic Electrophiles

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