Rh(III)-Catalyzed Relay Double Carbenoid Insertion and Diannulation of Sulfoximine Benzamides with α-Diazo Carbonyl Compounds: Access to Furo[2,3-<i>c</i>]isochromenes

Yang, Chen; Chen, Chen; Li, Shun-Fan; He, Xinwei; Zuo, Yuegang; Hu, Wangcheng; Zhou, Tongtong; Wang, Jian; Shang, Yongjia

doi:10.1021/acs.orglett.9b04659

Cited by 22 publications

(8 citation statements)

References 68 publications

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“…Recently in 2020, the groups of Shang and Wang reported a Rh(III)-catalyzed formation of furo[2,3-c]isochromene scaffolds via the coupling of sulfoximine benzamides and α-diazoβ-ketoesters (Scheme 44). [142] The mechanism proceeds through a relay catalysis allowing tandem double carbenoid insertion followed by annulation. Intermolecular competition experiments suggest the involvement of electrophilic CÀ H bond activation in the reaction mechanism, with a decrease of product yield observed upon increasing the electron-withdrawing ability of the para substituent on benzamide.…”

Section: Synthesis Of Chromone Derivatives Via Cà O Bond Annulationsmentioning

confidence: 99%

Transition‐Metal‐Catalyzed C−H Bond Functionalization of Arenes/Heteroarenes via Tandem C−H Activation and Subsequent Carbene Migratory Insertion Strategy

Jha

Khot

Kapur

2021

The Chemical Record

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The past decade has witnessed tremendous developments in transition-metal-catalyzed CÀ H bond activation and subsequent carbene migratory insertion reactions, thus assisting in the construction of diverse arene/heteroarene scaffolds. Various transition-metal catalysts serve this purpose and provide efficient pathways for an easy access to substituted heterocycles. A brief introduction to metal-carbenes has been provided along with key mechanistic pathways underlying the coupling reactions. The purpose of this review is to provide a concise knowledge about diverse directing group-assisted coupling of varied arenes/heteroarenes and acceptoracceptor/donor-acceptor diazo compounds. The review also highlights the synthesis of various carbocycles and fused heterocycles through diazo insertion pathways, via CÀ C, CÀ N and CÀ O bond forming reactions. The mechanism usually involves a CÀ H activation process, followed by diazo insertion leading to subsequent coupling.

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Section: Synthesis Of Chromone Derivatives Via Cà O Bond Annulationsmentioning

confidence: 99%

Transition‐Metal‐Catalyzed C−H Bond Functionalization of Arenes/Heteroarenes via Tandem C−H Activation and Subsequent Carbene Migratory Insertion Strategy

Jha

Khot

Kapur

2021

The Chemical Record

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“…Recently, Shang and co‐workers described a rhodium catalyzed synthesis of fura [2,3‐c] isochromene scaffold ( 174 ) using sulfoximine benzamides ( 172 ) with α‐diazo carbonyl compounds ( 173 ) (Scheme 45). [56] This protocol consist tandem double carbenoid insertion and diannulation reactions. A wide range of N‐Aryl methyl phenyl sulfoximine derivatives containing electron‐donating and electron‐withdrawing groups were employed with ethyl diazoacetate as a coupling partner under the optimized reaction conditions (1 equiv.…”

Section: Rh(iii)‐catalyzed Reactionsmentioning

confidence: 99%

Rhodium‐Catalyzed Cascade Reactions using Diazo Compounds as a Carbene Precursor to Construct Diverse Heterocycles

2021

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Diazo compounds being used as a precursor of carbenes in synthetic chemistry by reacting them in different manners like photochemically, thermally or with metal catalysts. Further, the use of metals as a catalyst generates metallocarbenes in the reaction medium which has similar reactivity like free carbenes. In this context, a number of transition metal catalysts like Rh, Pd, Cu, Ru, Ir, Fe etc. have been employed to generate metal bound carbenes in the reaction medium. Among various metal catalyst, rhodium being used extensively in industry as well as in academia to catalyze a number of cascade transformations containing carbene insertion/transfer. In this review, we are covering the efforts made in the last five years toward the synthesis of highly important heterocyclic compounds such as isoquinoline, indoles, isocoumines, oxazoles, carbazoles etc. through rhodium catalysed cascade reactions containing carbene transfer as the vital step.

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“…At the outset of 2019, Wang and Shang group unveiled an impressive example of tandem double carbenoid insertion and diannulation of sulfoximine benzamides with α ‐diazo carbonyl compounds for effectively synthesizing the furo[2,3‐ c ]isochromene scaﬀolds 48 in good to moderate yields (Scheme 68). [83] They regarded MPS (methyl phenyl sulfoximine) as traceless directing group and demonstrated an efficient C−H alkylation/cyclization process for accessing the fused cyclic framework via the cooperative effect of 3 mol % [RhCp*Cl 2 ] 2 as catalyst, 20 mol % of AgSbF 6 and 50 mol % of AgOAc at 70 °C in DCE as solvent. The group also proposed a presumptive catalytic cycle which is outlined in Scheme 68.…”

Section: C−h Functionalizationsmentioning

confidence: 99%

N−H and C−H Functionalization of Sulfoximine: Recent Advancement and Prospects

2020

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Sulfoximine and its congeners are a versatile class of structural motifs widely found in a plethora of pharmaceutical compounds and crop protection industries due to their fascinating structural architecture. Former discoveries nicely demonstrates the synthetic routes of unmasked and various N-functionalized sulfoximines but recent efforts from the synthetic community have divulged the applicability of sulfoximine analogue as reusable and transformable DG (directing group) to fabricate multifunctionalized (Het)arenes and enhance the bioactivities. Considering the synthetic potentiality and great influence of this scaffold, we provide a summary of NÀ H/CÀ H functionalization strategies of sulfoximine and application (as a directing group) with special emphasis on the mechanistic underpinnings. Additionally, we also hoped that this comprehensive review article (up to midst of 2020) will be useful for synthetic researchers and medicinal chemists and will inspire for further novel chemical transformations in this arena.

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Rh(III)-Catalyzed Relay Double Carbenoid Insertion and Diannulation of Sulfoximine Benzamides with α-Diazo Carbonyl Compounds: Access to Furo[2,3-c]isochromenes

Cited by 22 publications

References 68 publications

Transition‐Metal‐Catalyzed C−H Bond Functionalization of Arenes/Heteroarenes via Tandem C−H Activation and Subsequent Carbene Migratory Insertion Strategy

Transition‐Metal‐Catalyzed C−H Bond Functionalization of Arenes/Heteroarenes via Tandem C−H Activation and Subsequent Carbene Migratory Insertion Strategy

Rhodium‐Catalyzed Cascade Reactions using Diazo Compounds as a Carbene Precursor to Construct Diverse Heterocycles

N−H and C−H Functionalization of Sulfoximine: Recent Advancement and Prospects

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