Copper-catalyzed cascade annulation between α-bromocarbonyls and biaryl or (Z)-arylvinylacetylenes enabling a direct synthesis of dibenzocycloheptanes and related compounds

Electrooxidative-induced synthesis of structurally diverse seleno-dibenzocyclohepten-5-ones and seleno-spiro[5.5]trienones by selenylative carbannulation of biaryl ynones with diaryl diselenide has been developed. The switchable reactivity, intramolecular ortho-annulation or dearomative ipso-annulation, is directed by the substituent present on the ortho-aryl group of arylynone. The prominent features of this method include metal-free, external chemical oxidant-free conditions, and readily accessible substrates.Article pubs.acs.org/joc

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“…7-Phenyl-6-(phenylselanyl)-9-(trifluoromethoxy)-5H-dibenzo-[a,c] [7]annulen-5-one (3j). Yellow solid, 119 mg, 76% yield, m.p.…”

Section: ■ Conclusionmentioning

confidence: 99%

“…7-Phenyl-8-(phenylselanyl)-9H-benzo [6,7]cyclohepta[1,2-a]naphthalen-9-one (3m). Yellow oil, 103 mg,.…”

Section: ■ Conclusionmentioning

confidence: 99%

Electrochemical Selenylative Carbannulation of Biaryl Ynones to Seleno-Dibenzocycloheptenones/Spiro[5.5]Trienones

Reddy

Kolgave

2021

J. Org. Chem.

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“…By adopting similarc hemistry,t he same authors achieved a radicalb icyclization reactionb etween a-bromo g,d-unsaturated carbonyl compounds andb iaryl acetylenes. [49] This reaction, which was catalyzed by ac opper/bpy system in the presence of Na 2 CO 3 ,g ave as eries of new cycloheptene-fused polycyclic scaffolds (105). This radicalt ransformation was also successfully applied to (Z)-arylvinylacetylenes.…”

Section: Bicyclization Reactions Of Reactants With Radical Donor-accementioning

confidence: 99%

Recent Advances in Radical‐Enabled Bicyclization and Annulation/1,n‐Bifunctionalization Reactions

Huang

Hao

Jiang

2018

Chemistry An Asian Journal

141

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Over the past few years, the development of new radical reactions has gained considerable momentum. Most such radical transformations heavily depend on the in situ generation of reactive radical species, initiated by oxidants, metal salts, visible-light photocatalysis, or electrocatalysis. In this context, numerous radical-enabled bicyclization and annulation/1,n-bifunctionalization reactions have been developed, thereby providing efficient synthetic strategies for the assembly of functionalized cyclic rings that contain both heterocyclic and isocyclic skeletons. In this Focus Review, we highlight recent progress in this rapidly growing area by presenting a series of catalytic oxidative reactions, along with their reaction mechanisms and applications.

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“…They also achieved a copper‐catalyzed cascade annulation of γ,δ‐unsaturated α‐bromocarbonyls with biaryl or ( Z )‐arylvinylacetylenes for the construction of dibenzocycloheptanes and related compounds in moderate to high yields (Scheme ) . By using this method, cycloheptane and cycloheptene‐fused polycyclic scaffolds can easily be synthesized in one pot to give a rare 7‐ endo‐trig radical cyclization.…”

Section: Functionalization Of Alkynesmentioning

confidence: 99%

Developments in the Chemistry of α‐Carbonyl Alkyl Bromides

Ouyang

Song

2018

Chemistry An Asian Journal

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α-Carbonyl alkyl bromides are powerful reactive species for the formation of carbon-carbon bonds. Strategies relying on intermolecular C-H functionalization and cross-coupling reactions, also referred to as intramolecular cyclization, have been employed for the construction of alkenes, alkanes, ketones, and other natural-product-like ring compounds from simple alkynes, alkenes, and 1,n-enynes. In view of the importance of these α-carbonyl alkyl bromides, especially the difluoro carbonyl alkyl bromides, many researchers have focused their efforts to develop facile and mild synthetic methods for compounds with important biological activities. This review aims to briefly discuss the latest developments in the transformation of α-carbonyl alkyl bromides with emphasis on the related reaction mechanisms.

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Copper-catalyzed cascade annulation between α-bromocarbonyls and biaryl or (Z)-arylvinylacetylenes enabling a direct synthesis of dibenzocycloheptanes and related compounds

Cited by 18 publications

References 48 publications

Electrochemical Selenylative Carbannulation of Biaryl Ynones to Seleno-Dibenzocycloheptenones/Spiro[5.5]Trienones

Electrochemical Selenylative Carbannulation of Biaryl Ynones to Seleno-Dibenzocycloheptenones/Spiro[5.5]Trienones

Recent Advances in Radical‐Enabled Bicyclization and Annulation/1,n‐Bifunctionalization Reactions

Developments in the Chemistry of α‐Carbonyl Alkyl Bromides

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