Pd‐catalyzed homocoupling of arylhydrazines via C―N cleavage under O<sub>2</sub>

Yao, Peng

doi:10.1002/aoc.3108

Cited by 21 publications

(9 citation statements)

References 62 publications

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“…With respect to the mechanism, as reported in the literature, biaryl skeleton can be accessed by metal-catalyzed oxidative homo-coupling of aryl hydrazine 36 . In order to determine if our reaction proceeds through the aryl hydrazine intermediate, two control experiments were carried out (Fig.…”

Section: Resultsmentioning

confidence: 99%

N2H4 as traceless mediator for homo- and cross- aryl coupling

Qiu

et al. 2018

Nat Commun

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Transition-metal catalyzed couplings of aryl halides or arenes with aryl organometallics, as well as direct reductive coupling of two aryl halides, are the predominant methods to synthesize biaryls. However, stoichiometric amounts of metals are inevitably utilized in these reactions, either in the pre-generation of organometallic reagents or acting as reductant in situ, thus producing quantitative metal waste. Herein, we demonstrate that this longstanding challenge can be overcome with N2H4 as a metal surrogate. The fundamental innovation of this strategy is that N2 and H2 are generated as side products, which readily escape from the system after the reaction. The success of both homo- and cross-coupling of various aryl electrophiles bearing a wide range of functional groups manifests the powerfulness and versatility of this strategy. Furthermore, both homo- and cross-couplings of a series of alkaloids, amino acids and steroids exemplify application of this protocol in the functionalization of biologically active molecules.

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Section: Resultsmentioning

confidence: 99%

N2H4 as traceless mediator for homo- and cross- aryl coupling

Qiu

et al. 2018

Nat Commun

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“…In cross‐coupling arylation. Recent advances in the coupling reactions of arylhydrazine, which is utilized as an effective arylation partner in oxidative radical arylation and Pd‐catalyzed cross‐coupling (Heck‐type, Suzuki‐type, addition, homocoupling, etc …”

Section: Introductionmentioning

confidence: 99%

“…In cross-coupling arylation. Recent advances in the coupling reactions of arylhydrazine, which is utilized as an effective arylation partner in oxidative radical arylation [43][44][45][46][47][48][49][50] and Pd-catalyzed crosscoupling (Heck-type, [51][52][53][54] Suzuki-type, [55][56][57][58] addition, [59,60] homocoupling, [61][62][63] etc. [64][65][66][67][68][69][70][71][72][73] ) via C-N bond cleavage.…”

Section: Introductionmentioning

confidence: 99%

Denitrogenative Pd/Cu‐catalyzed Suzuki‐type Cross‐coupling of Aryltrifluoroborates with Arylhydrazine Hydrochlorides in Water under Room Temperature

Wang

Meng

Deng

et al. 2017

Applied Organom Chemis

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A water‐soluble palladium‐catalyzed Suzuki‐type cross‐coupling of aryltrifluoroborates with arylhydrazide hydrochlorides was efficiently developed under mild and environmentally benign conditions, in water without any ligand. The newly developed Pd/Cu co‐catalyzed denitrogenative reaction gave a range of structurally diverse substituted biaryls with good to excellent yields, in which the byproduct was nitrogen.

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“…In 2014, Kuang et al 16 reported a single example for the Pd(0)-catalyzed coupling of phenylhydrazine with phenyl triethoxysilane under 100 o C in the yield of 62%, which could not rule out the possibility of homocoupling by phenylhydrazine or phenylsilane. 17 Herein, we wish to report a novel approach to obtain diaryl derivatives with high selectivity and reactivity from arylhydrazines and aryl silanes via Pd-catalyzed denitrogenative cross-coupling with selective C-N bond cleavage of arylhydrazines in the presence of CSA (camphorsulfonic acid) under mild conditions.…”

Section: Introductionmentioning

confidence: 99%