Tellurium-promoted stereoselective hydrodebromination of 1,1-dibromoalkenes: synthesis of (E)-bromoalkenes

Perin, Gelson; Barcellos, Angelita M.; Peglow, Thiago J.; Nobre, Patrick C.; Cargnelutti, Roberta; Lenardão, Eder J.; Marini, Francesca; Santi, Claudio

doi:10.1039/c6ra24295b

Cited by 4 publications

(4 citation statements)

References 62 publications

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“…Solution state UV–visible spectra were measured with a Shimadzu UV-3600 spectrophotometer, and fluorescence spectra were measured using a Edison RF-5301PC spectrofluoremeter. Starting materials 2i , 2j , 2k , 2z , and 2za were synthesized following literature protocols.…”

Section: Methodsmentioning

confidence: 99%

“…23 Colorless liquid (yield: 198.6 mg, 46%); 1 (E)-2-(2-Bromovinyl)pyridine (2i). 25 Prepared according to a procedure reported by Gelson, Perin, and co-workers; yellow liquid (yield: 164.7 mg, 45%); 1 H NMR (400 MHz, CDCl 3 ) δ 8.54 (d, J = 4.7 Hz, 1H), 7.65 (td, J = 7.7, 1.8 Hz, 1H), 7.39 (d, J = 13.7 Hz, 1H), 7.21−7.16 (m, 2H), 7.14 (d,J = 13.7 Hz,1H).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

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Palladium-Catalyzed Domino Reaction for Stereoselective Synthesis of Multisubstituted Olefins: Construction of Blue Luminogens

et al. 2018

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The first Pd-catalyzed multicomponent reaction of aryl iodides, alkenyl bromides, and strained alkenes has been developed, which allowed us to synthesize a variety of multisubsituted olefins in yields of 45-96% with excellent stereoselectivity. The configuration of the product was controlled by the configuration of the alkenyl bromides. Moreover, this practical methodology employing readily available substrates was found to be tolerant to a wide range of functional groups. Fifty six examples of highly stereoselective tri- or tetrasubstituted olefins have been successfully synthesized via this methodology. Most of the synthesized tetrasubstituted olefins are good aggregation-induced emission (AIE) luminogens.

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Section: Methodsmentioning

confidence: 99%

Section: ■ Experimental Sectionmentioning

confidence: 99%

Palladium-Catalyzed Domino Reaction for Stereoselective Synthesis of Multisubstituted Olefins: Construction of Blue Luminogens

et al. 2018

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“…Recently, Ni and co‐workers described the reaction of 1,1‐dibromoalkenes with several thiols in a basic media to afford selectively sulfanyl alkynes in good yields. More recently, we described the synthesis of ( E )‐1‐bromo‐1‐selenanylalkenes and ketene selenanylacetals, and ( E )‐bromostyrenes starting from 1,1‐dibromoalkenes. Considering the versatility of the electrophilic cyclization approach to access 3‐functionalized benzo[ b ]selenophenes, we envisioned that 1‐(2‐organylchalcogenylethynyl)‐2‐butylselenanylbenzenes 3 could be a suitable starting material to this reaction.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 2‐Organylchalcogenyl–benzo[b]selenophenes: 1‐(2,2‐Dibromovinyl)‐2‐butylselenanylbenzenes as Precursors to Access Alkynes Susceptible to Cyclization

et al. 2017

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A convenient synthesis of 1‐(2‐organylchalcogenylethynyl)‐2‐butylselenanylbenzenes was established taking advantage of the selective reaction of 1‐(2,2‐dibromovinyl)‐2‐butylselenanylbenzenes with thiols or diorganyl diselenides. The new 1‐(2‐chalcogenylethynyl)‐2‐butylselenanylbenzenes were prepared in good yields and used as precursors of 2‐organylchalcogenylbenzo[b]selenophenes via electrophilic cyclization using I2, Br2 or PhSeBr as electrophiles. Different classes of new 3‐substituted‐ (3‐iodo, 3‐bromo, 3‐phenylselenanyl) benzo[b]selenophenes were prepared in good yields. The synthetic application of the obtained products was demonstrated employing the benzo[b]selenophenes in Suzuki and Sonogashira cross‐coupling reactions.

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“…As desilylations can happen easily in alcoholic solvents under basic conditions, it is obvious that deprotection of the TMS group might be the first step in the reaction of 1i with Na 2 Te/NaHTe in ethanol. Furthermore, monodebromination of geminal dibromo-cyclopropanes and 1,1-dibromoalkenes can occur smoothly with telluride salts (Na 2 Te/NaHTe) in ethanol even at 50 °C. , It is expected that monodebromination might be the next step in the reaction of 1i with telluride salts at 75 °C. Therefore, desilylated and monodebrominated product 3i′ would be the key intermediate in the reaction of 1i and telluride salts in ethanol at 75 °C ( 3 , Scheme ).…”

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confidence: 99%

Cascade and Effective Syntheses of Functionalized Tellurophenes

2018

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A one-pot and transition-metal-catalyst-free synthetic strategy to construct functionalized tellurophenes has been developed. Substituted 1,1-dibromo-1-en-3-ynes are smoothly converted to tellurophenes with telluride salts in high yield via a series of cascade reactions through reductive debromination, hydrotelluration, nucleophilic cyclization, and aromatization. Close inspection of the results clearly showed that the reactivity of in situ prepared telluride salts are significantly influenced by the polarity of the solvent system and the electronic nature of the substituent on the enyne substrate. This method reports the first direct synthesis of 3-aryltellurophenes in high yields at room temperature. This novel reaction strategy is also found to be a promising synthetic method for multisubstituted tellurophenes and selenophenes.

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Tellurium-promoted stereoselective hydrodebromination of 1,1-dibromoalkenes: synthesis of (E)-bromoalkenes

Cited by 4 publications

References 62 publications

Palladium-Catalyzed Domino Reaction for Stereoselective Synthesis of Multisubstituted Olefins: Construction of Blue Luminogens

Palladium-Catalyzed Domino Reaction for Stereoselective Synthesis of Multisubstituted Olefins: Construction of Blue Luminogens

Synthesis of 2‐Organylchalcogenyl–benzo[b]selenophenes: 1‐(2,2‐Dibromovinyl)‐2‐butylselenanylbenzenes as Precursors to Access Alkynes Susceptible to Cyclization

Cascade and Effective Syntheses of Functionalized Tellurophenes

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