Pd‐Catalyzed Tandem Coupling Reaction of 2‐<i>gem</i>‐Dibromovinylanilines and <i>N</i>‐Tosylhydrazones to Construct 2‐(1‐phenylvinyl)‐indoles

Song, Jian; Chi, Xiaochen; Meng, Long; Zhao, Pingping; Sun, Fenggang; Zhang, Daopeng; Jiao, Luyang; Liu, Qing; Dong, Yunhui; Liu, Hui

doi:10.1002/adsc.201900230

Cited by 10 publications

(3 citation statements)

References 69 publications

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“…Song et al [43] developed the synthesis of 2-(1-phenylvinyl)-indoles via the novel Pd(0)-catalyzed intermolecular coupling reaction of 2-gem-dibromovinylanilines and Ntosylhydrazones (Figure 4). Reaction conditions were optimized, (PdCl 2 (PPh 3 ) 2 was chosen as a catalyst, and tBuOLi was chosen as a base (the other bases were DMAP, tBuOK, TEA, CsCO 3 , and CsF)).…”

Section: Coupling Tandem Processesmentioning

confidence: 99%

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Recent Progress in Pd-Catalyzed Tandem Processes

Nikoshvili

Matveeva

2023

Catalysts

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In recent years, Pd-containing catalytic systems for tandem processes have gained special attention due to their enhanced catalytic properties and their possibility of performing several reactions without the necessity of separating the intermediates. In this review, recent progress in Pd-catalyzed tandem processes is considered. Three types of catalytic systems are described: homogeneous catalysts (including immobilized Pd complexes); heterogeneous catalysts supported on oxides, MOFs, COFs, etc., with particular attention to the supports containing acid/base sites; and metal-enzyme catalysts for chemoenzymatic tandem processes applied in fine organic synthesis and biotechnology. For homogeneous Pd-catalyzed reactions, different tandem reactions were considered, i.e., cross-coupling, cyclization, carbonylation, isomerization, alkylation, arylation, etc.

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Section: Coupling Tandem Processesmentioning

confidence: 99%

“…Subsequently, alkylpalladium species were formed with carbene intermediate generated from the diazo compound. Finally, β-H elimination allowed for the synthesis of the desired product and the regeneration of Pd(0) [43].…”

Section: Coupling Tandem Processesmentioning

confidence: 99%

Recent Progress in Pd-Catalyzed Tandem Processes

Nikoshvili

Matveeva

2023

Catalysts

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“…On the basis of our recently developed cyclization of allenamides, [52][53][54][55][56][57][58][59][60] we envisioned a plausible Csp 3 -H bond activation of the allylic position, which might undergo hydrogen atom transfer to deliver pyrroline derivates as shown in Scheme 1D. However, the chemo-and regio-selectivity and low BDE distinction between the old and new CÀ H bond are the main challenging.…”

Section: Introductionmentioning

confidence: 99%

Palladium‐Catalyzed Cycloisomerization of 1,6‐Allene‐Ene via [1,8]‐Sigmatropic Hydrogen Shift of Allylic C−H

Chen,

Tian,

Liang

et al. 2023

Asian J Org Chem

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A ligand‐free palladium‐promoted [1,8]‐sigmatropic hydrogen shift reaction of 1,6‐allene‐ene was reported, which went through an intramolecular Ene cyclization using base as a hydrogen shuttle. Notably, the transformation could realize the HAT process via the hydrogen shift from an old allylic C‐H bond to a new one in the presence of oxidant, between which have low BDE distinction. The mild reaction conditions, high atom economy and good chemo/regioselectivity proved the valuable of this strategy. The control experiments using acetone‐D6/D2O proved that neither solvent nor water were involved in the cycloisomerization process and HAT process was more convincible. The target products could achieve more valuable molecules via convenient synthetic transformation.

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Recent Advances in Transition‐Metal‐Catalyzed Reactions of N‐Tosylhydrazones

2021

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Transition‐metal‐catalyzed reactions of N‐tosylhydrazones provide a convenient access to various molecules by novel carbon‐carbon or carbon‐heteroatom bond formations via carbene‐type intermediates. The present review highlights recent developments in the field emphasize of the employment of different transition metals as catalysts, synthetic applications, mechanistic studies and use in domino and multicomponent reactions.

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Pd‐Catalyzed Tandem Coupling Reaction of 2‐gem‐Dibromovinylanilines and N‐Tosylhydrazones to Construct 2‐(1‐phenylvinyl)‐indoles

Cited by 10 publications

References 69 publications

Recent Progress in Pd-Catalyzed Tandem Processes

Recent Progress in Pd-Catalyzed Tandem Processes

Palladium‐Catalyzed Cycloisomerization of 1,6‐Allene‐Ene via [1,8]‐Sigmatropic Hydrogen Shift of Allylic C−H

Recent Advances in Transition‐Metal‐Catalyzed Reactions of N‐Tosylhydrazones

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