Palladium-catalyzed denitrogenative Hiyama cross-coupling with arylhydrazines under air

Zhang, Hui; Wang, Chunjie; Li, Zhiwei; Zi-yun, Wang

doi:10.1016/j.tetlet.2015.06.095

Cited by 30 publications

(11 citation statements)

References 87 publications

(11 reference statements)

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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%

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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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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“…1 20 Following the general procedure on 0.4 mmol scale with IMes Me ·HCl (10 mol%) as a ligand, the title compound was obtained as a light yellow liquid (45% yield). 1 26 Following the general procedure on 0.4 mmol scale with IMes Me ·HCl (10 mol%) as a ligand, the title compound was obtained as a white solid (51% yield), m.p.= 33 -34 ºC (lit. 35 -36 ºC).…”

Section: Analytic Data Of the Reductive Productsmentioning

confidence: 99%

Nickel-catalyzed C–N bond reduction of aromatic and benzylic quaternary ammonium triflates

Yang

Zhai

et al. 2016

Chem. Commun.

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A nickel-catalyzed, efficient C-N bond reduction of aromatic and benzylic ammonium triflates has been developed using sodium isopropoxide as a reducing agent. The high efficiency, mild conditions, and good compatibility with various substituents made this method an effective supplement to the current catalytic hydrogenation reactions. Combining this reductive deamination reaction with directed aromatic functionalization reactions, a powerful strategy for regioselective functionalization of arenes was demonstrated using dialkylamine groups as traceless directing groups.

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“…Arylhidrazines 32 could be efficiently used as substrates for the palladium‐catalyzed oxidative cross‐coupling with the trimethoxysilane 9 in the presence of camphorsulfonic acid (CSA) and TBA, so the corresponding coupling products 8 were isolated (Scheme ) 39…”

Section: Arylation Reactionsmentioning

confidence: 99%

The Hiyama Cross‐Coupling Reaction: New Discoveries

Foubelo

Nájera

Yus

2016

The Chemical Record

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ABSTRACT:In this review article recent developments in the Hiyama cross-coupling reaction from 2010 up today are presented. The most important methodology involves formation of biaryl systems by using aryl bromides or iodides and aryl trialkoxy silanes: other variants are far less studied. The most useful procedures are collected paying special attention to the synthetic application of this methodology in synthetic organic chemistry.

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Palladium-catalyzed denitrogenative Hiyama cross-coupling with arylhydrazines under air

Cited by 30 publications

References 87 publications

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

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

Nickel-catalyzed C–N bond reduction of aromatic and benzylic quaternary ammonium triflates

The Hiyama Cross‐Coupling Reaction: New Discoveries

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