Palladium-Catalyzed Hiyama Coupling of Benzylic Ammonium Salts via C–N Bond Cleavage

Han, Chao; Zhang, Zhenming; Xu, Silin; Wang, Kai; Chen, Kaiting; Zhao, Junfeng

doi:10.1021/acs.joc.9b02554

Cited by 29 publications

(10 citation statements)

References 73 publications

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“…In the case of aryl trimethoxysilanes, the substrate containing electron-donating groups afforded corresponding diarylmethane derivatives in (57–97%) yield range. Moreover, the substrate-bearing heterocycles, including thiophene and furan, gave coupling products a 94% yield [ 109 ].…”

Section: Palladium Chloride As Catalystmentioning

confidence: 99%

Transition Metal Catalyzed Hiyama Cross-Coupling: Recent Methodology Developments and Synthetic Applications

et al. 2022

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Hiyama cross-coupling is a versatile reaction in synthetic organic chemistry for the construction of carbon–carbon bonds. It involves the coupling of organosilicons with organic halides using transition metal catalysts in good yields and high enantioselectivities. In recent years, hectic progress has been made by researchers toward the synthesis of diversified natural products and pharmaceutical drugs using the Hiyama coupling reaction. This review emphasizes the recent synthetic developments and applications of Hiyama cross-coupling.

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Section: Palladium Chloride As Catalystmentioning

confidence: 99%

Transition Metal Catalyzed Hiyama Cross-Coupling: Recent Methodology Developments and Synthetic Applications

et al. 2022

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“…The first example of the Pd-catalyzed Hiyama coupling reaction of benzyl ammonium salts with aryl silanes was reported by our group in 2019 (Scheme 29). [44] The key to the success of this coupling was the use of TBAF as the additive; other fluoride salts (KF, AgF, and CsF) failed to promote this transformation. Various functional groups were all well tolerated, including OMe, F, CN, and CO 2 tBu.…”

Section: Reactions With Aryl Silanesmentioning

confidence: 99%

Recent Advances in the Pd‐Catalyzed Coupling of Arylhydrazines and Ammonium Salts via C−N Bond Cleavage

Zhao

2021

The Chemical Record

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Both arylhydrazines and quaternary ammonium salts are readily accessible or commercially available chemicals that show versatile reactivity in Pd-catalyzed coupling reactions via CÀ N bond cleavage. A tremendous array of coupling reactions involving reaction partners such as organoborons, aryl silanes, alkenes, alkynes, arylation or alkylation reagents in CÀ H functionalization and carbonylation reactions are summarized, in which arylhydrazines or quaternary ammonium salts function as aryl or alkyl donors. This account mainly focuses on recent advances in Pd-catalyzed coupling reactions with arylhydrazines or quaternary ammonium salts via CÀ N bond cleavage, including mechanistic elucidations.

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“…Later, this type of coupling was accomplished with aryltrimethylammonium triflates using either a palladium- or an iron-based catalyst . In a similar manner, quaternary aryl- or benzylammonium salts have been used in Negishi, Stille, Suzuki–Miyaura, Sonogashira, Buchwald–Hartwig, Murahashi, and Hiyama cross-coupling reactions or with organoaluminum reagents (Scheme ). The general mechanism of these reactions typically involves (i) oxidative addition of the C–N bond of the quaternary ammonium salt 1 , 4 , 7 , 10 , 13 , 16 , 19 , 22 , or 25 to the TM, resulting in cleavage of the C–N bond; (ii) transmetalation with the organometallic compound 2 , 5 , 8 , 17 , 20 , or 23, alkyne 11 or 26 , or amine 14 ; and (iii) reductive elimination to afford products 3 , 6 , 9 , 12 , 15 , 18 , 21 , 24 and 27 .…”

Section: C–n Bond Activation Via Quaternization Of the Nitrogenmentioning

confidence: 99%

Recent Methodologies That Exploit Oxidative Addition of C–N Bonds to Transition Metals

2020

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The activation of σ-bonds by transition metals underpins a wide range of methods for the synthesis of complex molecules. Within this context, C–N bond activation has emerged recently as a powerful strategy for the preparation or utilization of nitrogen-containing compounds, due to the prevalence of C–N bonds in organic compounds. A key challenge in this area is that most C–N bonds are relatively inert, and this makes their activation a difficult task. Since the turn of the millennium the number of published articles regarding C–N bond activation has grown exponentially, providing important improvements in methodologies for such transformations. Indeed, several distinct strategies have been developed to achieve C–N bond activation. The most common have exploited either strain release or quaternization of the nitrogen center, while other state-of-the-art strategies, such as oxidative addition of neutral C–N bonds and the use of directing groups, have also appeared. Despite considerable progress, deeper insight into the mechanisms of activation and improvements in atom economy are still required for the field to advance. In this Perspective we give an overview of key advances in catalytic methodologies where C–N bond activation is achieved by oxidative addition to transition metals.

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Palladium-Catalyzed Hiyama Coupling of Benzylic Ammonium Salts via C–N Bond Cleavage

Cited by 29 publications

References 73 publications

Transition Metal Catalyzed Hiyama Cross-Coupling: Recent Methodology Developments and Synthetic Applications

Transition Metal Catalyzed Hiyama Cross-Coupling: Recent Methodology Developments and Synthetic Applications

Recent Advances in the Pd‐Catalyzed Coupling of Arylhydrazines and Ammonium Salts via C−N Bond Cleavage

Recent Methodologies That Exploit Oxidative Addition of C–N Bonds to Transition Metals

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