Pd-Catalyzed Highly Regio- and Stereoselective Formation of C–C Double Bonds: An Efficient Method for the Synthesis of Benzofuran-, Dihydrobenzofuran-, and Indoline-Containing Alkenes

Gao, Yang; Xiong, Wenfang; Chen, Huoji; Wu, Wanqing; Peng, Jianwen; Gao, Yuan; Jiang, Huanfeng

doi:10.1021/acs.joc.5b01024

Cited by 70 publications

(21 citation statements)

References 68 publications

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“…In this reaction, the alkyl palladium species generated in situ participates in the following carbene coupling reaction to produce the olefination product (Scheme b). Other cascade intramolecular carbopalladation/ N -tosylhydrazone-based carbene coupling reactions were also reported afterward. , Very recently, Zhao and co-workers developed a palladium-catalyzed sp 3 C–H bond olefination reaction of silyl naphthyl bromide with N -tosylhydrazone . The reaction has been proposed to involve an unusual aryl to alkyl 1,5-palladium migration process, which is followed by carbene coupling to furnish the olefination product (Scheme c).…”

Section: Olefination Of Ketones Aldehydes and Beyondmentioning

confidence: 99%

Transition-Metal-Catalyzed Cross-Coupling with Ketones or Aldehydes via N-Tosylhydrazones

2020

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Ketones and aldehydes play central roles in organic synthesis. There are numerous broadly used reactions that are related to the carbonyl reactivity, such as Grignard reactions, Wittig reactions, aldol reactions, and so on. In addition, the formation of enol triflates is a classic protocol that enables the ketones to be applied in transition-metal-catalyzed cross-coupling reactions, in which case the ketones are considered as the precursors of alkenyl electrophiles in the C−C bond-forming transformations. In the past decade, a new type of ketone-or aldehyde-based C−C bond-forming transformations has emerged. In this type of reactions, the ketones or aldehydes are first converted to their corresponding N-tosylhydrazones, which are employed as reaction partners in various transition-metal-catalyzed carbene-based cross-coupling reactions. The N-tosylhydrazone-based carbene couplings significantly enhance the potential of ketones and aldehydes in modern organic synthesis. This Perspective aims to give an overview of carbene coupling reactions with N-tosylhydrazones from the viewpoint of exploring new potentials of ketones and aldehydes in organic synthesis.

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Section: Olefination Of Ketones Aldehydes and Beyondmentioning

confidence: 99%

Transition-Metal-Catalyzed Cross-Coupling with Ketones or Aldehydes via N-Tosylhydrazones

2020

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“…[92] Next to the work from the group of Valdés, a selective formation of CÀ C double bonds was published by the group of Jiang (Scheme 67). [93] This reaction allowed for the synthesis of dihydrobenzofuran-( 12), indoline-( 13) and benzofuran-containing alkenes (14,15). By choosing a proper functionalization of the N-tosylhydrazone, a highly regio-and stereoselective reaction could be achieved.…”

Section: Palladium Catalyzed Formation Of Multiple Bondsmentioning

confidence: 99%

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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“…Substituents at the benzene moiety often originate from the synthetic precursor used to construct the benzofuran scaffold. Synthetic methods for assembling the benzofuran scaffold have typically involved acid-catalyzed cyclizations [11][12][13][14][15][16][17], carbonylative cyclizations via Sonogashira reactions [18][19][20][21][22][23][24], Heck-type cyclizations [25][26][27][28][29], photocyclizations [30][31][32][33][34], radical cyclizations [35][36][37][38][39], and other types of transition-metal catalyzed transformations [40][41][42][43][44][45]. When it comes to the functionalization of the furan part, there exists a considerable number of methods for directly functionalizing either the C2 or C3 position [46][47][48][49][50][51][52][53][54][55][56].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Elaborate Benzofuran-2-Carboxamide Derivatives through a Combination of 8-Aminoquinoline Directed C–H Arylation and Transamidation Chemistry

et al. 2020

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Herein, we present a short and highly modular synthetic route that involves 8-aminoquinoline directed C–H arylation and transamidation chemistry, and which enables access to a wide range of elaborate benzofuran-2-carboxamides. For the directed C–H arylation reactions, Pd catalysis was used to install a wide range of aryl and heteroaryl substituents at the C3 position of the benzofuran scaffold in high efficiency. Directing group cleavage and further diversification of the C3-arylated benzofuran products were then achieved in a single synthetic operation through the utilization of a one-pot, two-step transamidation procedure, which proceeded via the intermediate N-acyl-Boc-carbamates. Given the high efficiency and modularity of this synthetic strategy, it constitutes a very attractive method for generating structurally diverse collections of benzofuran derivatives for small molecule screening campaigns.

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Pd-Catalyzed Highly Regio- and Stereoselective Formation of C–C Double Bonds: An Efficient Method for the Synthesis of Benzofuran-, Dihydrobenzofuran-, and Indoline-Containing Alkenes

Cited by 70 publications

References 68 publications

Transition-Metal-Catalyzed Cross-Coupling with Ketones or Aldehydes via N-Tosylhydrazones

Transition-Metal-Catalyzed Cross-Coupling with Ketones or Aldehydes via N-Tosylhydrazones

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

Synthesis of Elaborate Benzofuran-2-Carboxamide Derivatives through a Combination of 8-Aminoquinoline Directed C–H Arylation and Transamidation Chemistry

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