Bromination of naphthalene and derivatives: High temperature bromination XI

Daştan, Arif; Tahir, Muhammad Nawaz; Ülkü, D.; Balcı, Metin

doi:10.1016/s0040-4020(99)00758-9

Cited by 25 publications

(22 citation statements)

References 23 publications

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“…Recently, we showed that thermal and photobromination of decalin (1) gave trans,trans,trans -2,5,7,9-tetrabromooctalin (2) as the major product along with smaller amounts of bromonaphthalene derivatives (Scheme 1). [19][20] It was remarkable that the reaction proceeded with high regio-and stereoselectivity. Although the calculations demonstrated that the most stable tetrabromide, 2, was formed exclusively, it may well be that this is also a kinetically controlled product.…”

Section: Introductionmentioning

confidence: 99%

High temperature bromination Part XXIII: Bromination of octahydro-1H-indene and octahydro-1H-4,7-methanoindene

Özer¹,

Kılbaş²,

Balcı³

2013

Arkivoc

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Thermal and photobromination of octahydro-1H-indene and octahydro-1H-4,7-methanoindene were investigated. Three isomeric tetrabromides (1,3,4,7-tetrabromo-2,3,4,5,6,7-hexahydro-1H-indene) were formed along with a smaller amount of tribromoindane and a pentabromide by thermal bromination of octahydro-1H-indene. The thermodynamically most stable isomers were formed. Morover, thermal and photochemical bromination of octahydro-1H-4,7-methanoindene furnished bromides resulting regiospecifically from the allylic bromination of the five-membered ring. Furthermore, the double bond formed as the intermediate functional group was also brominated due to its pyramidalization. The mechanism proposed for the formation of product distribution was discussed.

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Section: Introductionmentioning

confidence: 99%

High temperature bromination Part XXIII: Bromination of octahydro-1H-indene and octahydro-1H-4,7-methanoindene

Özer¹,

Kılbaş²,

Balcı³

2013

Arkivoc

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“…For example, while photobromination of naphthalene leads to trans,trans,trans-tetrabromide 4, 9a photobromination of 1,4-dibromonaphthalene 2 affords compound 3. 10 On the other hand, bromination of naphthalene 1 at -30 ºC produces compound 2.…”

Section: Introductionmentioning

confidence: 99%

Functionalization of naphthalene: a novel synthetic route to brominated naphthoquinones

Çakmak¹,

Akar²,

Kaplan³

2012

Arkivoc

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An efficient procedure is described for synthesis of 2,5,8-tribromonaphthoquinone (12) from naphthalene in four reaction steps. Silver-promoted solvolysis of hexabromide 3 produces the specific diastereostereoisomer 10. Dehydrobromination of 10 using sodium methoxide gives tribromodihydronaphthalene-1,4-diol 11 in high yield. PCC oxidation of either 10 or 11 results in the formation of 2,5,8-tribromonaphthalene-1,4-dione (12).

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“…[5] Addition of electrophiles to 1,8-dilithionaphthenes generated from 1-bromonaphthalenes by lithium-halogen exchange and subsequent deprotonation is asecond approach (Scheme 1a), but this method is limited to the formation of products containing identical peri-substituents and limited to reactants containing functional groups that tolerate organolithium reagents. Electrophilic aromatic substitution of 1-substituted naphthalenes is one approach to synthesize peri-disubstituted naphthalenes (Scheme 1a), but low yields of the 1,8-substituted products are obtained because of poor regioselectivity.…”

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confidence: 99%

“…To identify conditions for the Ir-catalyzed, peri-borylation of CÀHb onds in 1-hydrosilyl naphthalenes,w ec onducted reactions of 1-dimethylhydrosilyl naphthalene 1a with B 2 pin 2 catalyzed by iridium complexes derived from [Ir(cod)OMe] 2 and N,N-donor ligands L1-L5 in THF at 80 8 8C ( Table 1, entries [1][2][3][4][5]. Reactions with 3,4,7,8-tetramethyl phenanthroline L5 formed product 2a in higher yield (61 %) than those with 4,4'-di-tert-butyl bipyridine L1 and phenanthroline ligands L2-L4 (up to 47 %).…”

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confidence: 99%

Iridium‐Catalyzed, Silyl‐Directed, peri‐Borylation of C−H Bonds in Fused Polycyclic Arenes and Heteroarenes

Hartwig

2018

Angew Chem Int Ed

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peri-Disubstituted naphthalenes exhibit interesting physical properties and unique chemical reactivity, due to the parallel arrangement of the bonds to the two peri-disposed substituents. Regioselective installation of a functional group at the position peri to 1-substituted naphthalenes is challenging due to the steric interaction between the existing substituent and the position at which the second one would be installed. We report an iridium-catalyzed borylation of the C-H bond peri to a silyl group in naphthalenes and analogous polyaromatic hydrocarbons. The reaction occurs under mild conditions with wide functional group tolerance. The silyl group and the boryl group in the resulting products are precursors to a range of functional groups bound to the naphthalene ring through C-C, C-O, C-N, C-Br and C-Cl bonds.

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Bromination of naphthalene and derivatives: High temperature bromination XI

Cited by 25 publications

References 23 publications

High temperature bromination Part XXIII: Bromination of octahydro-1H-indene and octahydro-1H-4,7-methanoindene

High temperature bromination Part XXIII: Bromination of octahydro-1H-indene and octahydro-1H-4,7-methanoindene

Functionalization of naphthalene: a novel synthetic route to brominated naphthoquinones

Iridium‐Catalyzed, Silyl‐Directed, peri‐Borylation of C−H Bonds in Fused Polycyclic Arenes and Heteroarenes

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