Synthesis of 1-Cyano-3-acylnaphthalenes via Formal [4+2] Benzannulation of 2-(2-Alkynylphenyl)acetonitriles and Alkynones

Chen, Lulu; Zhang, Jingwen; Yang, Wan-Wan; Fu, Ji‐Ya; Zhu, Jun‐Yan; Wang, Yan‐Bo

doi:10.1021/acs.joc.9b00948

Cited by 23 publications

(10 citation statements)

References 74 publications

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“…The synthesis of polysubstituted naphthalenes (Scheme 14) was investigated by Wang et al [20] The expected product was obtained with 56% yield. Further experiments for screening of the reaction have been performed and it was found that a higher yield of the product was obtained with 10 mol% loading of LiO t Bu, and hence, it is considered as the ideal condition for the reaction.…”

Section: Carbon-carbon Bond Forming Reactionsmentioning

confidence: 99%

Roles of Alkali Metals tert‐Butoxide as Catalysts and Activators in Organic Transformations

et al. 2023

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The alkali metal tert‐butoxides have found wide application as catalysts and activators for the conversion of numerous organic molecules. These formidable additives in catalytic amounts are extensively employed in the transition metal‐free approaches to serve for the single‐electron transfer processes towards the formation of C−C and C‐heteroatom bond formation. This review elucidates their multifaceted roles encompassing a series of novel synthetic methodologies, in‐depth analyses of their reactivity patterns, and catalytic efficiencies across a myriad of reactions. The involvement of alkali metal tert‐butoxides either directly or in combination with other metals as catalysts are discussed along with the detailed mechanistic pathways in various reactions. Overall, this article summarises approximately all reactions those have been influenced by the catalytic amounts of tert‐butoxides and reported in the last decades.

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Section: Carbon-carbon Bond Forming Reactionsmentioning

confidence: 99%

Roles of Alkali Metals tert‐Butoxide as Catalysts and Activators in Organic Transformations

et al. 2023

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“…And MK‐0633, [12] is a promising 5‐lipoxygenase inhibitor ( Scheme 1 ,a ). Over the past decades, many efforts have been made to construct such motifs [5,6,13–21] . However, the development of general and efficient methodologies remains challenging and is still highly desired.…”

Section: Introductionmentioning

confidence: 99%

Fe‐Catalyzed Intramolecular Cross‐Dehydrogenative Arylation (CDA), Efficient Synthesis of 1‐Arylnaphthalenes and 4‐Arylcoumarins

Liu

Diao

Wang

et al. 2021

Helvetica Chimica Acta

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Direct cross-dehydrogenative coupling of different inert CÀ H bonds is the most straightforward and environmentally benign method to construct CÀ C bonds. In this paper, we developed an iron-catalyzed intramolecular cross-dehydrogenative arylation (CDA) between benzylic C(sp 3 )H bond and aromatic C(sp 2 )H bond. From the readily available linear substrates, 1-arylnaphthalenes and 4-arylcoumarins can be quickly constructed with moderate to good yield (18 examples, up to 73 % yield) in one step. Both symmetrical and unsymmetrical substrates with different functional groups could tolerate this system well to form the anticipated products. A radical initiated dehydrogenative cyclization-dehydrogenation tandem process was proposed.

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“…11 In 2007, the Deng group reported the base-mediated [4+2] benzannulation of vinyl malononitriles and nitroolefins. 12 Since then, various types of benzannulation such as [3+2+1], 13,14 [3+3], 15–17 and [4+2] 18 have been uncovered. As an alternative, Wang 19 and Ye 20 groups independently reported a benzannulation route by N -heterocyclic carbene catalysis.…”

Section: Introductionmentioning

confidence: 99%

Regioselective synthesis of benzonitriles via amino-catalyzed [3+3] benzannulation reaction

Jiang¹,

Jin²,

Yu³

et al. 2020

Journal of Chemical Research

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A straightforward synthesis of benzonitriles is achieved via amino-catalyzed [3+3] benzannulation of α,β-unsaturated aldehydes and 4-arylsulfonyl-2-butenenitriles. Using pyrrolidine as an organocatalyst via iminium activation, a series of substituted benzonitriles were obtained in good to high yields in a regioselective manner. This reaction can proceed smoothly under mild reaction conditions and without the aid of any metals, additional oxidants, or strong bases, thus making this an efficient and environmentally friendly method to access benzonitriles.

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Synthesis of 1-Cyano-3-acylnaphthalenes via Formal [4+2] Benzannulation of 2-(2-Alkynylphenyl)acetonitriles and Alkynones

Cited by 23 publications

References 74 publications

Roles of Alkali Metals tert‐Butoxide as Catalysts and Activators in Organic Transformations

Roles of Alkali Metals tert‐Butoxide as Catalysts and Activators in Organic Transformations

Fe‐Catalyzed Intramolecular Cross‐Dehydrogenative Arylation (CDA), Efficient Synthesis of 1‐Arylnaphthalenes and 4‐Arylcoumarins

Regioselective synthesis of benzonitriles via amino-catalyzed [3+3] benzannulation reaction

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