Substrate-Controlled Generation of 3-Sulfonylated 1-Indenones and 3-Arylated (<i>Z</i>)-Indenes via Cu-Catalyzed Radical Cyclization Cascades of <i>o</i>-Alkynylbenzonitriles

Sulfonyl hydrazides are widely used as organic reagents. Advances in the past decade are summarized in the following categories by key intermediates: (1) [RO2S.]; (2) RO2SSR; (3) [ArS.]; (4) [RO2S−]; (5) RSO2‐[Metal] species; (6) Ar‐[Metal] species; (7) RSX; (8) RS‐DBU; (9) nucleophilic amino group; (10) sulfonyl hydrazides as diazene or sulfinic acid surrogate. Reactions with alkenes, alkynes, aldehydes, alcohols, thiophenol, Grignard reagents, among others, are discussed. We hope this review will promote future research in this area.

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“…Jiang and co‐workers used ortho ‐alkynyl benzonitriles as reactants in the radical dicyclizaiton with sulfonyl hydrazides (Eq. 33‐1,2).…”

Section: Sulfonyl Radiacls‐mediated Reactionsmentioning

confidence: 99%

Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

et al. 2020

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“…When o-cyanoarylalkyl acetylenes 407 were used as starting reagents as well as amount of TBHP increased and the reaction was carried out without addition of water, 3aryl (Z)-indenes 409 were formed (Scheme 180). [226] Other methods for the synthesis of 3-sulfonyl indenones from o-alkynyl benzonitriles and sulfonyl hydrazides are based on the usage of the CuI/TBHP [227] system or Na 2 S 2 O 8 [228] in MeCNÀ H 2 O at 60°C. In all cases, in the first step of the process, sulfonyl radical A is generated under oxidative conditions.…”

Section: Construction Of Carbocyclesmentioning

confidence: 99%

Oxidative Sulfonylation of Multiple Carbon‐Carbon bonds with Sulfonyl Hydrazides, Sulfinic Acids and their Salts

et al. 2020

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Oxidative coupling methodology is widely applied for the formation of carbon-carbon and carbon-heteroatom bonds. This review focuses on methods for oxidative sulfonylation of multiple bonds involving sulfonyl hydrazides, sulfinic acids and their salts as sulfonylation reagents. Under oxidative conditions, they generate sulfonyl radicals, trapped by multiple carbon-carbon bonds resulting in a variety of SO 2-containing products: mainly, vinyl and alkynyl sulfones, hydroxy-, keto, and halo-substituted sulfones, sulfonylated derivatives of carbo-and heterocycles. This exhaustive review summarizes 321 references from 1996 to 2020 with the specialization of the studies of the last five years, and is divided into the chapters according to the classes of compounds being sulfonylated.

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“…Both 3‐sulfonylated 1‐indenones 129 and 3‐arylated indenes 130 were synthesized with a novel approach developed by Zhu et al The combination of copper(II) with tert ‐butyl hydroperoxide (TBHP) as a catalytic oxidative system was able to promote radical cyclization cascades o‐ alkynylbenzonitriles 127 with sulfonyl hydrazides 128 . The chemoselectivity of this reaction depends on the substituents at the alkynyl unit of o‐ alkynylbenzonitriles.…”

Section: Transition Metal (Tm)‐catalyzed Processesmentioning

confidence: 99%

Recent Advances in the Synthesis of Indenes

2019

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Indenes constitute an important class of molecules which continue to attract interest from the synthetic organic chemists′ community because not only many natural and synthetic compounds embodying the indene skeleton display bioactivity or pharmaceutical activity but also because indenes find applications in material science, e.g. in photovoltaic solar cells and in the preparation of new fluorescent materials, and in the preparation of metal complexes with special catalytic activity. Many approaches have been exploited in the last four years to build this bicyclic system, the two most explored being cationic processes involving an intramolecular Friedel‐Crafts reaction and those in which a transition metal plays a key role in assembling the indene framework. In this review the results of the synthetic efforts toward indenes made in the 2016–2019 period are reviewed.

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Substrate-Controlled Generation of 3-Sulfonylated 1-Indenones and 3-Arylated (Z)-Indenes via Cu-Catalyzed Radical Cyclization Cascades of o-Alkynylbenzonitriles

Cited by 44 publications

References 71 publications

Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

Oxidative Sulfonylation of Multiple Carbon‐Carbon bonds with Sulfonyl Hydrazides, Sulfinic Acids and their Salts

Recent Advances in the Synthesis of Indenes

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