Palladium-catalyzed dearomative 1,4-arylmethylenation of naphthalenes

Zhang, Enshen; Chen, Chen; Wang, Xueling; Wang, Jian; Shang, Yongjia

doi:10.1039/d2qo00266c

Cited by 5 publications

(3 citation statements)

References 60 publications

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“…[133] The method developed by Shang, Wang, and co-workers allowed the synthesis of spirooxindoles via dearomative 1,4arylmethylenation of naphthalenes in the coupling of naphthamides 31 and N-tosylhydrazones using PdCl 2 and SPhos ligand L35 to produce derivatives 32 containing an E-exocyclicdouble-bond. [134] Major characteristics include medium to high yields and exclusive formation of the E isomers (Scheme 110). A key π-allyl-palladium species (int-51) was suggested to be involved in product formation upon reacting with tosylhydrazones and the resulting alkyl-palladium intermediate delivers spirooxindoles.…”

Section: Chemistryselectmentioning

confidence: 99%

“…The method developed by Shang, Wang, and co‐workers allowed the synthesis of spirooxindoles via dearomative 1,4‐arylmethylenation of naphthalenes in the coupling of naphthamides 31 and N ‐tosylhydrazones using PdCl 2 and SPhos ligand L 35 to produce derivatives 32 containing an E ‐exocyclic‐double‐bond [134] . Major characteristics include medium to high yields and exclusive formation of the E isomers (Scheme 110).…”

Section: Condensed Bicyclic Moleculesmentioning

confidence: 99%

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Recent Advances in the Synthesis of Five‐membered Nitrogen Heterocycles Induced by Palladium Ions and Complexes

Molnár

2023

ChemistrySelect

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This review aims to collect and analyze recent results with respect to the use of varied palladium preparations in the synthesis of five-membered nitrogen heterocycles including condensed derivatives. Results have been selected with focus on studies of the last three years. Furthermore, a common feature of all methods treated here is that the nitrogencontaining five-membered ring is formed via ring closing of appropriate starting materials. Selected examples discussed will reveal that a plethora of products from small monocycles to condensed multi-ring systems can be successfully accessed. Major features are wide product ranges, high product yields and stereoselectivities often achieved under mild reaction conditions.

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Section: Chemistryselectmentioning

confidence: 99%

Section: Condensed Bicyclic Moleculesmentioning

confidence: 99%

Recent Advances in the Synthesis of Five‐membered Nitrogen Heterocycles Induced by Palladium Ions and Complexes

Molnár

2023

ChemistrySelect

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“…[ 7 , 8 , 9 , 10 , 11 ] The current pathways for Pd‐catalyzed dearomatization of (hetero)arenes are mostly two‐electron processes, requiring harsh reaction conditions, such as high temperature, to overcome the energy barrier of the dearomative insertion step. The preference for more active (hetero)arenes and fused aromatic rings, [ 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 ] instead of nonactivated phenyl rings, represents the present state of Pd‐catalyzed dearomatizations ( Scheme 1 a ). Recently, visible light‐induced radical pathways have provided benign methods for the dearomatization of a broader scope of (hetero)arenes including a few examples of nonactivated phenyl rings.…”

Section: Introductionmentioning

confidence: 99%

Radical‐Dearomative Generation of Cyclohexadienyl Pd(II) toward the 3D Transformation of Nonactivated Phenyl Rings

Fan,

Jiang,

Liu

et al. 2023

Advanced Science

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Traditional palladium‐catalyzed dearomatization of (hetero)arenes takes place via an ionic pathway and usually requires elevated temperatures to overcome the energy barrier of the dearomative insertion step. Herein, a combination of the radical and two‐electron pathways is disclosed, which enables room temperature dearomative 3D transformations of nonactivated phenyl rings with Pd(0) as the catalyst. Experimental results together with density functional theory (DFT) calculations indicate a versatile π‐allyl Pd(II) species, cyclohexadienyl Pd(II), possibly is involved in the dearomatization. This species is generated by combining the cyclohexadienyl radical and Pd(I). The cyclohexadienyl Pd(II) provides chemoselective (carboamination and trieneylation), regioselective (1,2‐carboamination), and diastereoselective (carbonyl‐group directed face selectivity) conversions.

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Stereoselective Three‐Component Construction of Conjugated 1,3‐Dienes via Palladium‐Catalyzed Alkene/Allene/Carbenoid Insertion Cascade

et al. 2023

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A three component construction of conjugated 1,3-dienes bearing oxindoles or isoquinolinediones from alkenylated aryl iodides, allenes and diazo compounds via a palladium catalyzed sequential alkene/allene/carbenoid insertion reaction was developed. Three CÀ C bonds were formed in high order, offering access to multi-substituted dienes in high yields and up to > 20:1 E/Z selectivities. The reaction features excellent functional groups tolerance under mild conditions.

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Palladium-catalyzed dearomative 1,4-arylmethylenation of naphthalenes

Cited by 5 publications

References 60 publications

Recent Advances in the Synthesis of Five‐membered Nitrogen Heterocycles Induced by Palladium Ions and Complexes

Recent Advances in the Synthesis of Five‐membered Nitrogen Heterocycles Induced by Palladium Ions and Complexes

Radical‐Dearomative Generation of Cyclohexadienyl Pd(II) toward the 3D Transformation of Nonactivated Phenyl Rings

Stereoselective Three‐Component Construction of Conjugated 1,3‐Dienes via Palladium‐Catalyzed Alkene/Allene/Carbenoid Insertion Cascade

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