Modern methods for the synthesis of substituted naphthalenes

Koning, Charles B. de; Rousseau, Amanda L.; Otterlo, Willem A. L. van

doi:10.1016/s0040-4020(02)01424-2

Cited by 227 publications

(78 citation statements)

References 222 publications

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“…Although many methods have been devised for the synthesis of substituted naphthalenes,13 the oxidative photocyclization of 1‐aryl‐1,3‐butadienes has scarcely been developed 14. This is in striking contrast to the similar oxidative photocyclization of stilbenes, which has been extensively studied and applied to the synthesis of phenanthrenes 15.…”

Section: Introductionmentioning

confidence: 99%

A Combined Transition‐Metal‐Catalyzed and Photopromoted Process: Synthesis of 2,3‐Fused 4‐Phenylnaphthalen‐1‐yl Carboxylates from 1,7‐Diaryl‐1,6‐diynes

Yamamoto

Mori

Shibuya

2015

Chemistry A European J

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2,3-Fused 4-phenylnaphthalen-1-yl carboxylates were synthesized in a step- and atom-economical manner using a ruthenium-catalyzed hydrocarboxylative cyclization of 1,7-diaryl-1,6-diynes and subsequent oxidative photocyclization. The scope of this novel two-step process was demonstrated by the construction of diverse structures from substrates with various tethers and terminal aryl groups. Late-stage CH functionalizations of the arylnaphthalene product further enhance the synthetic potential of the developed process.

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Section: Introductionmentioning

confidence: 99%

A Combined Transition‐Metal‐Catalyzed and Photopromoted Process: Synthesis of 2,3‐Fused 4‐Phenylnaphthalen‐1‐yl Carboxylates from 1,7‐Diaryl‐1,6‐diynes

Yamamoto

Mori

Shibuya

2015

Chemistry A European J

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“…For example, the DA reactions 6 of benzynes appended with an alkyl (R 1 Me, t Bu, Table 1, entries 5 and 6), 7a,b a carbamoyl (R 1 CONEt 2 , entry 7), 7c or a nitro group (R 1 NO 2 , entry 8) 7g at the 3 position provided mixtures of the proximal and distal adducts in varying ratios, and their regioselectivities were hardly predictable, although those having inductively electron withdrawing groups, such as uoro (R 1 F, entries 1 and 2) 7d and alkoxy groups (R 1 OMe, entries 3 and 4), 7e,f produced cycloadducts with good to excellent proximal selectivities.…”

Section: Introductionmentioning

confidence: 99%

Experimental and Theoretical Studies on Regiocontrol of Benzyne Reactions Using Silyl and Boryl Directing Groups

Ikawa

Tokiwa

Akai

2012

J. Synth. Org. Chem. Jpn.

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Abstract:The silyl and boryl directed regiocontrol of benzyne reactions and their theoretical analyses using density functional theory (DFT) are described herein. The Diels Alder reactions of both 3 silyl and 3 borylbenzynes with substituted furans and the [3 2] cycloadditions of 3 silylbenzynes with 1,3 dipoles predominantly produced distal cycloadducts, whereas the [3 2] cycloadditions of the borylbenzynes exclusively produced proximal cycloadducts. Moreover, primary amines selectively underwent nucleophilic addition reactions at the more hindered ortho position of the silyl group of the benzynes. The origin of these anomalous regiochemistries was theoretically evaluated using the natural bond orbital and reaction pathway analyses including the transition states of these reactions. On the basis of DFT calculations, it is proposed that the reactions of the borylbenzynes were controlled by the electrostatic effect of the boryl group, whereas those of the silylbenzynes were primarily governed by the steric effect of the silyl group.

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“…Differently substituted naphthalene derivatives have played an important role in the chemical and pharmaceutical industries1 as well as in the fields of optical and electronic materials 2. The development of new and efficient methodologies for the synthesis of polysubstituted naphthalene derivatives has recently attracted much attention 3. Traditionally, the regioselective construction of polysubstituted aromatic compounds has been carried out by the stepwise introduction of substituents through electrophilic substitutions4 or coupling reactions 5,6.…”

Section: Introductionmentioning

confidence: 99%

An Efficient Synthesis of Polysubstituted Naphthalene Derivatives by Gold‐Catalyzed Cyclization of 1‐Arylalka‐2,3‐dienyl Acetates

Kong

2010

Eur J Org Chem

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An efficient synthetic strategy to generate differently polysubstituted naphthalenes and iodonaphthalenes through a gold‐catalyzed cyclization reaction of 1‐arylalka‐2,3‐dienyl acetates was described. Due to the substituent loading capability of both the aromatic ring and the allene moiety, different substituents may be introduced to the different locations of the naphthalenes. A possible mechanism of the reaction involving the formation of alkenyl and naphthyl Au species was proposed on the basis of the mechanistic study.Iodination of the gold species afforded iodonaphthalenes, which are useful building blocks to introduce molecular complexity and diversity by coupling reactions.

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Modern methods for the synthesis of substituted naphthalenes

Cited by 227 publications

References 222 publications

A Combined Transition‐Metal‐Catalyzed and Photopromoted Process: Synthesis of 2,3‐Fused 4‐Phenylnaphthalen‐1‐yl Carboxylates from 1,7‐Diaryl‐1,6‐diynes

A Combined Transition‐Metal‐Catalyzed and Photopromoted Process: Synthesis of 2,3‐Fused 4‐Phenylnaphthalen‐1‐yl Carboxylates from 1,7‐Diaryl‐1,6‐diynes

Experimental and Theoretical Studies on Regiocontrol of Benzyne Reactions Using Silyl and Boryl Directing Groups

An Efficient Synthesis of Polysubstituted Naphthalene Derivatives by Gold‐Catalyzed Cyclization of 1‐Arylalka‐2,3‐dienyl Acetates

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