Cascade Rh(<scp>ii</scp>) and Yb(<scp>iii</scp>) catalyzed synthesis of substituted naphthofurans <i>via</i> transannulation of <i>N</i>-sulfonyl-1,2,3-triazoles with β-naphthols

Kaladevi, Selvam; Kamalraj, M.; Altia, Minakshi; Rajasekar, Shanmugam; Anbarasan, Pazhamalai

doi:10.1039/c8cc10306b

Cited by 29 publications

(10 citation statements)

References 43 publications

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“…A similar but step-economic approach to access benzofurans was reported by Kang and co-workers through Rh(II)- and Cu(I)-catalyzed sequential sp 3 C–H insertion and aerobic oxidation (path C) . A Rh(II)-catalyzed O–H insertion followed by Yb(III)-catalyzed cyclization and oxidation sequence of triazoles and phenols was reported by Anbarasan and co-workers for the synthesis of benzo/naphthofurans (path D) . Despite these efficient methods, the development of novel synthetic methods for the construction of benzofurans is still desirable, and herein, we report a new protocol to prepare benzofurans via a Rh(II)-catalyzed denitrogenative cascade process.…”

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confidence: 84%

Rh(II)-Catalyzed Denitrogenative Transannulation of N-Sulfonyl-1,2,3-triazolyl Cyclohexadienones for the Synthesis of Benzofurans and Cyclopropa[cd]indole-carbaldehydes

2019

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A rhodium-catalyzed intramolecular denitrogenative transannulation of N-sulfonyl-1,2,3-triazole-tethered cyclohexadienones has been achieved for the synthesis of benzofurans and cyclopropa[cd]indole-carbaldehydes in an operationally simple procedure. Remarkably, the reaction pathway is fully dependent on the linker heteroatom (O or N) present between the cyclohexadienone unit and triazole moiety. In the case of O-linked triazoles, a cascade sequence consisting of intramolecular cyclopropanation and rearrangement takes place, leading to the formation of benzofurans, while, in the case of N-linked triazoles, cyclopropa[cd]indole-carbaldehydes were isolated exclusively.

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confidence: 84%

Rh(II)-Catalyzed Denitrogenative Transannulation of N-Sulfonyl-1,2,3-triazolyl Cyclohexadienones for the Synthesis of Benzofurans and Cyclopropa[cd]indole-carbaldehydes

2019

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“…Subsequently, in 2019, we reported the cascade Rh(II) and Yb(III)-catalyzed synthesis of naphthofurans 62 from ßnaphthol 61 and triazoles 45 in the presence of oxygen atmosphere (Scheme 12). [24] The reaction goes through initial OÀ H insertion to generate 63 in the presence of rhodium catalyst followed by enamide and imine tautomerization delivers the imine 64. Formation of product 62 was rationalized through ytterbium-catalyzed cyclization of imine to give 64 followed by aromatization-cum-oxidation in the presence of molecular oxygen.…”

Section: Reaction With Oxygen Nucleophilesmentioning

confidence: 99%

Catalytic Functionalization of Metallocarbenes Derived from α‐Diazocarbonyl Compounds and Their Precursors

Yadagiri

Anbarasan

2021

The Chemical Record

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Short and efficient synthesis of heterocyclic compounds are highly desirable in synthetic organic chemistry. It is a dream approach to accomplish these syntheses from readily available starting materials in a single step. In this personal account, we discuss our contribution in the synthesis of heterocyclic compounds and beyond from N-sulfonyl-1,2,3-triazoles and αdiazocarbonyl compounds, which are the precursors for α-imino (carbonyl) metal carbenes in the presence of transition metal catalysts. Functionalization of α-imino(carbonyl) metal carbenes has been achieved through in-situ generated metal-stabilized ylides followed by either intramolecular trapping by non-polar bonds, rearrangement, cycloaddition, or 1,3-insertion fashion, which led to the efficient synthesis of various synthetically important intermediates and heterocyclic compounds.

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“…In 2019, Anbarasan group demonstrated that azavinyl carbene could also be inserted into the OÀ H bond of βnaphthols 124 for the construction of substituted naphthofurans 127 (Scheme 28). [47] The one-pot dual catalytic cascade process involved Rh(II) catalyzed 1,3-insertion of carbene into the OÀ H bond followed by Yb(III) catalyzed intramolecular annulation and subsequent aerial oxidation to access an array of 1-aminonaphthofurans in moderate to good yields. The reaction scope was broad as various triazoles and β-naphthols/ phenols could be used in this reaction.…”

Section: Oà H Nà H Insertionmentioning

confidence: 99%

Catalytic Insertion Reactions of α‐Imino Carbenoids

Pal

Volla

2021

The Chemical Record

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Over the past decade, α-imino carbenoids generated via transition metal (such as rhodium, nickel, copper, palladium, silver) catalyzed denitrogenative ring-opening of N-sulfonyl-1,2,3-triazoles have found an extensive account of applications in synthetic organic chemistry. Particularly, they have been widely utilized as a donor/acceptor carbene complex in a range of transformations leading to diverse nitrogen containing compounds and heterocycles. Along the same direction, 3-diazoindolin-2-imines were successfully applied as an alternative source of αimino carbenoid precursors for the development of a number of methodologies to access diverse indole derivatives. This review summarizes the insertion reactions of α-imino metal carbenes derived from N-sulfonyl-1,2,3-triazoles and 3-diazoindolin-2-imines.

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Cascade Rh(ii) and Yb(iii) catalyzed synthesis of substituted naphthofurans via transannulation of N-sulfonyl-1,2,3-triazoles with β-naphthols

Abstract: Synthesis of substituted naphthofurans has been achieved via an efficient cascade Rh(ii)/Yb(iii) catalyzed transannulation of N-sulfonyl-1,2,3-triazoles with β-naphthols.

Cited by 29 publications

References 43 publications

Rh(II)-Catalyzed Denitrogenative Transannulation of N-Sulfonyl-1,2,3-triazolyl Cyclohexadienones for the Synthesis of Benzofurans and Cyclopropa[cd]indole-carbaldehydes

Rh(II)-Catalyzed Denitrogenative Transannulation of N-Sulfonyl-1,2,3-triazolyl Cyclohexadienones for the Synthesis of Benzofurans and Cyclopropa[cd]indole-carbaldehydes

Catalytic Functionalization of Metallocarbenes Derived from α‐Diazocarbonyl Compounds and Their Precursors

Catalytic Insertion Reactions of α‐Imino Carbenoids

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