Silver‐Catalyzed One‐Pot Access to Diastereoselective Benzo[5,6]oxepino[2,3‐<i>c</i>]pyrroles <i>via</i> Formal (5+2)‐Annulation of Donor‐/Acceptor‐Type Aryl Vinyl Diazosuccinimide with Ketones

Laha, Debasish; Meher, Kajal B.; Bankar, Onkar S.; Bhat, Ramakrishna G.

doi:10.1002/ajoc.202200062

Cited by 4 publications

(3 citation statements)

References 56 publications

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“…A silver catalyzed one-pot protocol for the diastereoselective synthesis of dihydrobenzoxepines has been recently reported by Bhat group. [190] Silver(I) triflimide was found to be an efficient catalyst for the formal [5 + 2] cycloaddition to access dihydrobenzoxepines as a single diastereomer using vinyl-diazo-succinimides as 5-C-synthons and ketones. Novel cycloaddition protocol was found to be highly regio-, chemo-and diastereo selective as evidenced by preparation of fluorosubstituted dihydro-benzo [5,6] oxepino [2,-3c] pyrroles.…”

Section: Silver Catalysis In Cycloaddition Reactionsmentioning

confidence: 99%

“…Silver(I) triflimide catalyzed diastereoselective synthesis of dihydrobenzoxepines and examples of fluorine-containing products. [190] Scheme 38. Silver catalyzed enantioselective [3 + 3] cycloaddition reaction of activated isocyanides for the preparation of six-membered bicyclic 1,2,4triazine systems, [191] 1,2-diphenylethylenediamine phosphine-urea type trifluoromethyl group containing ligand used for preparation of Ag catalyst.…”

Section: Silver Catalysis In Cycloaddition Reactionsmentioning

confidence: 99%

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Application of Silver Compounds in Fluoroorganic Synthesis: A Minireview

2023

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The mini‐review is focused on application of silver and its compounds in fluoroorganic synthesis, and it reflects immense progress in this field which took place during the last two decades, with additional examples of reactivity of historical importance. Reactions of C−H, C−F, N−H and O−H bond functionalization, as well as catalysis of cycloaddition reactions and intramolecular rearrangement, retro‐rearrangement, and functional group migrations, have been described. Whenever available in original works, the reaction mechanisms were discussed. Since silver may be catalytically active in each of its available oxidation states from (0), via (I) and (II) to (III) with their immensely diverse properties, the organofluorine part is preceded by a brief overview of chemistry of silver in general. Uniqueness of silver among Group 11 elements is highlighted.

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Section: Silver Catalysis In Cycloaddition Reactionsmentioning

confidence: 99%

Section: Silver Catalysis In Cycloaddition Reactionsmentioning

confidence: 99%

Application of Silver Compounds in Fluoroorganic Synthesis: A Minireview

2023

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“…The chemoselectivity of the reaction depended on the type of the used alkynes. Silver triflimide AgNTf 2 33 was used in one of the stages of the synthesis of new fluorinated symmetric and asymmetric imidazolium salts, as well as of their complexes with various metals [72] and in the diastereoselective synthesis of benzo [5,6]oxepino [2,3-c]pyrroles via the [5 + 2]-annulation of the donor-acceptor type of arylvinyldiazosuccinimide with ketones [73]. The iodination reaction of a wide range of arenes (derivatives of anisole, aniline, acetanilide and phenol) in the presence of AgNTf 2 33 and N-iodosuccinimide is known [74].…”

Section: Agntf2mentioning

confidence: 99%

Triflamides and Triflimides: Synthesis and Applications

Moskalik

Astakhova

2022

Molecules

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Among the variety of sulfonamides, triflamides (CF3SO2NHR, TfNHR) occupy a special position in organic chemistry. Triflamides are widely used as reagents, efficient catalysts or additives in numerous reactions. The reasons for the widespread use of these compounds are their high NH-acidity, lipophilicity, catalytic activity and specific chemical properties. Their strong electron-withdrawing properties and low nucleophilicity, combined with their high NH-acidity, makes it possible to use triflamides in a vast variety of organic reactions. This review is devoted to the synthesis and use of N-trifluoromethanesulfonyl derivatives in organic chemistry, medicine, biochemistry, catalysis and agriculture. Part of the work is a review of areas and examples of the use of bis(trifluoromethanesulfonyl)imide (triflimide, (CF3SO2)2NH, Tf2NH). Being one of the strongest NH-acids, triflimide, and especially its salts, are widely used as catalysts in cycloaddition reactions, Friedel–Crafts reactions, condensation reactions, heterocyclization and many others. Triflamides act as a source of nitrogen in C-amination (sulfonamidation) reactions, the products of which are useful building blocks in organic synthesis, catalysts and ligands in metal complex catalysis, and have found applications in medicine. The addition reactions of triflamide in the presence of oxidizing agents to alkenes and dienes are considered separately.

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Umpolung Reactivity of Diazo Arylidene Succinimides: Distal C−H Functionalization of α‐Thiocarbonyls from the Reactive Carbenoid Center

Bankar,

Laha,

Meher

et al. 2023

Chemistry An Asian Journal

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Herein, for the first time we have explored the umpolung reactivity of the vinylogous carbon center of diazo arylidene succinimide (DAS) through rhodium catalysis to achieve [2,3]‐Stevens rearrangement of α‐thioether esters. The protocol has successfully demonstrated the distal C−H bond functionalization of the α‐thioether esters. Alongside, the carbenoid reactivity of DAS has also been achieved with Doyle‐Kirmse reaction of allyl/propargyl phenyl sulfides. The protocol proved to be practical to synthesize a wide variety of [2,3]‐Stevens rearrangement products exclusively and the possible side products emanating from Pummerer rearrangement and [1,2]‐Stevens rearrangement were not observed. This catalytic protocol works smoothly in environmentally benign solvent under open air to afford the corresponding desired products with excellent diastereo‐, regio‐ and chemo‐selectivities in good to excellent yields. The protocol also proved to be scalable on gram quantity.

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Silver‐Catalyzed One‐Pot Access to Diastereoselective Benzo[5,6]oxepino[2,3‐c]pyrroles via Formal (5+2)‐Annulation of Donor‐/Acceptor‐Type Aryl Vinyl Diazosuccinimide with Ketones

Cited by 4 publications

References 56 publications

Application of Silver Compounds in Fluoroorganic Synthesis: A Minireview

Application of Silver Compounds in Fluoroorganic Synthesis: A Minireview

Triflamides and Triflimides: Synthesis and Applications

Umpolung Reactivity of Diazo Arylidene Succinimides: Distal C−H Functionalization of α‐Thiocarbonyls from the Reactive Carbenoid Center

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