Iodonium ylides: an emerging and alternative carbene precursor for C–H functionalizations

Kumar, Sanjeev; Borkar, Vaishnavi; Mujahid, Md.; Nunewar, Saiprasad; Kanchupalli, Vinaykumar

doi:10.1039/d2ob01644c

Cited by 22 publications

(6 citation statements)

References 106 publications

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“…This carbonyl provides an interaction site to both nucleophiles [29,30] and electrophiles [31][32][33] in ketone form and tautomerized enol form, respectively. Thus, iodonium ylides can be used as a two-atom or three-atom surrogate, which makes it an important annulation partner in organic synthesis [29,33,34]. Iodonium ylides are used as annulation partners for the synthesis of various nitrogen-containing heterocycles [35][36][37][38].…”

Section: Iron-catalyzed Annulation Of 2-aminobenzaldehydes With Iodon...mentioning

confidence: 99%

Iron-Catalyzed Annulation of 2-Aminobenzaldehydes with Iodonium Ylides: A Mild and General Route for the Synthesis of Acridinone Derivatives

Joshi,

Dash,

Thirumoorthi

et al. 2024

ajc

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An inexpensive iron-catalyzed annulation of 2-aminobenzaldehydes with iodonium ylides for the synthesis of acridinone derivatives was reported. A library of biologically relevant 3,4-dihydropyridine-1-one scaffold was synthesized by the reaction of corresponding 2-amino benzaldehyde and iodonium ylides under mild reaction conditions in a green solvent. The reaction tolerates various alkyl, aryl and halogenated substrates and affords the desired product in moderate to good yields. The reported reaction has an inexpensive catalytic system, mild reaction conditions, easily accessible substrates and the use of green solvents.

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Section: Iron-catalyzed Annulation Of 2-aminobenzaldehydes With Iodon...mentioning

confidence: 99%

Iron-Catalyzed Annulation of 2-Aminobenzaldehydes with Iodonium Ylides: A Mild and General Route for the Synthesis of Acridinone Derivatives

Joshi,

Dash,

Thirumoorthi

et al. 2024

ajc

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“…Common carbene precursors do not fulfill our requirement, as functionalized diazo compounds are unstable. Ylides have been well-established as non-diazo carbene precursors in organic synthesis, [43][44][45] and recently, we have developed a sulfoxonium-iodonium hybrid ylide (I (III) / S (VI) -ylide) and studied its reactivity towards various unsaturated bonds. [46] Given the marked difference in leaving group ability between I (III) and S (VI) , [47,48] we envisioned that the I (III) /S (VI) -ylide might react with a transition-metal catalyst to yield a unique S + -substituted metal carbene with exceedingly high electrophilicity.…”

Section: Introductionmentioning

confidence: 99%

A Carbene Relay Strategy for Cascade Insertion Reactions

Li,

Mi,

Huang

et al. 2023

Angew Chem Int Ed

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Insertion reactions that involve stabilized electrophilic metallocarbenes are of great importance for installing α‐heteroatoms to carbonyl compounds. Nevertheless, the limited availability of carbene precursors restricts the introduction of only a single heteroatom. In this report, we describe a new approach based on an I(III)/S(VI) reagent that promotes the cascade insertion of heteroatoms. This is achieved by sequentially generating two α‐heteroatom‐substituted metal carbenes in one reaction. We found that this mixed I(III)/S(VI) ylide reacts efficiently with a transition metal catalyst and an X‐H bond (where X = O, N). This transformation leads to the sequential formation of a sulfoxonium‐ and an X‐substituted Rh‐carbenes, enabling further reactions with another Y‐H. Remarkably, a wide range of symmetrical and unsymmetrical α,α‐O,O‐, α,α‐O,N‐, and α,α‐N,N‐subsituted ketones can be prepared under mild ambient conditions. In addition, we successfully demonstrated other cascades, such as CN/CN double amidation, C‐H/C‐S double insertion, and C‐S/Y‐H double insertion (where Y = S, N, O, C). Notably, the latter two cascades enabled the simultaneous installation of three functional groups to the α‐carbon of carbonyl compounds in a single step. These reactions demonstrate the versatility of our approach, allowing for the synthesis of ketones and esters with multiple α‐heteroatoms using a common precursor.

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“…However, most of these approaches require the employment of stoichiometric amounts of external oxidants, and the assembly of α-pyrones in the absence of oxidants via NHC catalysis remains rare. Herein, we disclose an NHC catalyzed formal [3 + 3] cycloaddition reaction of α-bromo enals and 2-chlorocyclohexane-1,3-diones, giving efficient access to 4,5,6-trisubstituted α-pyrones 12 bearing various substituents and substitution patterns in generally good to excellent yields. It is worth noting that no external oxidant is needed in this process.…”

Section: Introductionmentioning

confidence: 99%

Oxidant free synthesis of α-pyronesviaan NHC-catalyzed [3 + 3] annulation of bromoenals with 2-chloro-1,3-diketones

Luo

et al. 2022

Org. Biomol. Chem.

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Iodonium ylides: an emerging and alternative carbene precursor for C–H functionalizations

Abstract: This review article summarizes the synthesis of iodonium ylides and its potential applications in C–H funtionalizations/annulations, including nitrogen heterocycles, oxygen heterocyles, alkenylations, etc.

Cited by 22 publications

References 106 publications

Iron-Catalyzed Annulation of 2-Aminobenzaldehydes with Iodonium Ylides: A Mild and General Route for the Synthesis of Acridinone Derivatives

Iron-Catalyzed Annulation of 2-Aminobenzaldehydes with Iodonium Ylides: A Mild and General Route for the Synthesis of Acridinone Derivatives

A Carbene Relay Strategy for Cascade Insertion Reactions

Oxidant free synthesis of α-pyronesviaan NHC-catalyzed [3 + 3] annulation of bromoenals with 2-chloro-1,3-diketones

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