Modular construction of α-furanyl ketones <i>via</i> semi-pinacol rearrangement-mediated ring expansion

Chen, Yang; Zhu, Shifa

doi:10.1039/d2qo01324j

Cited by 6 publications

(1 citation statement)

References 62 publications

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“…The Zhu group developed an intramolecular domino process to synthesize α‐furanyl ketones 75 , involving furyl metal carbene formation and semi‐pinacol rearrangement, using conjugated enynals 74 (Scheme 28). [42] Using Pd(CH 3 CN) 2 Cl 2 or PtCl 2 , the alkyne moiety in hydroxymethyl tethered enynal 74 is activated, followed by intramolecular 5‐exo‐dig cyclization to form furyl metal carbene I . A subsequent semi‐pinacol rearrangement generates zwitterionic intermediate II , which undergoes proto‐demetalation to yield product 75 .…”

Section: Furyl Metal Carbene X−h Insertion Reactions Using Enynones O...mentioning

confidence: 99%

Accessing Functionalized Furans from Reacting Enynones and Enynals through Furyl Metal Carbenes

Cho,

Kim

2024

Asian J Org Chem

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Enynones and enynals represent donor‐type carbene precursors that efficiently form furyl metal carbenes via a catalytic intramolecular 5‐exo‐dig cyclization and rearrangement cascade, in a 100% atom‐economical manner, using various metals. These furyl metal carbenes have been successfully utilized in numerous carbene reactions, including metal carbene X–H insertion, cyclopropanations, metathesis, and cross‐coupling, demonstrating a broad reaction scope and efficiency in constructing highly functionalized furans. Recent years have witnessed significant advancements in transformations involving furyl metal carbenes, especially in asymmetric carbene insertion reactions, domino reactions involving zwitterionic intermediates, various rearrangement strategies, and their application in synthesizing functional materials and drug candidates. In this review, we summarize recent progress in furyl metal carbene reactions generated from enynones and enynals, focusing on the synthesis of highly functionalized furans.

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Section: Furyl Metal Carbene X−h Insertion Reactions Using Enynones O...mentioning

confidence: 99%

Accessing Functionalized Furans from Reacting Enynones and Enynals through Furyl Metal Carbenes

Cho,

Kim

2024

Asian J Org Chem

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De Novo Synthesis of α‐Oligo(arylfuran)s and Its Application in OLED as Hole‐Transporting Material

Wei

Chen

Wang

et al. 2023

Chemistry A European J

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Tuning the photophysical properties of π-conjugated oligomers by functionalization of skeleton, to achieve an optically and electronically advantageous building block for organic semiconductor materials is a vital yet challenging task. In this work, a series of structurally well-defined polyarylfunctionalized α-oligofurans, in which aryl groups are introduced precisely into each of the furan units, are rapidly and efficiently synthesized by de novo metal-free synthesis of αbi(arylfuran) monomers for the first time. This new synthetic strategy nicely circumvents the cumbersome substituent introduction process in the later stage by the preinstallation of the desired aryl groups in the starting material. The characterization of α-oligo(arylfuran)s demonstrates that photoelectric properties of coplanar α-oligo(arylfuran)s can be tuned through varying aryl groups with different electrical properties. These novel α-oligo(arylfuran)s have good hole transport capacity and can function as hole-transporting layers in organic light-emitting diodes, which is indicative of significant breakthrough in the application of α-oligofurans materials in OLEDs. And our findings offer an avenue for the ingenious use of α-oligo(arylfuran)s as p-type organic semiconductors for OLEDs.

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Heterocycles from Donor and Donor/Donor Carbenes

Zhu

2023

Topics in Heterocyclic Chemistry

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Modular construction of α-furanyl ketones via semi-pinacol rearrangement-mediated ring expansion

Abstract: A simple and efficient semi-pinacol rearrangement reaction of enynals involving a metal carbene intermediate has been developed, which allows the efficient and practical synthesis of various functionalized α-furanyl ketones in...

Cited by 6 publications

References 62 publications

Accessing Functionalized Furans from Reacting Enynones and Enynals through Furyl Metal Carbenes

Accessing Functionalized Furans from Reacting Enynones and Enynals through Furyl Metal Carbenes

De Novo Synthesis of α‐Oligo(arylfuran)s and Its Application in OLED as Hole‐Transporting Material

Heterocycles from Donor and Donor/Donor Carbenes

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