Expedient Synthesis of Biologically Potent Aryloxycoumarins and (Aryloxyimino)ethylcoumarins via Copper(II)-Promoted Chan–Lam Coupling Reaction

Medda, Arunima; Pal, Gargi; Singha, Raghunath; Hossain, Tabassum; Saha, Achintya; Das, Asish R.

doi:10.1080/00397911.2011.594544

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2024

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Cited by 12 publications

(2 citation statements)

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“…Phenols could be used instead of amines (Table ) . The reaction of benzyl boronic acid pinacol ester ( 1a ) with phenol derivatives bearing an electron-donating or -withdrawing group gave the corresponding benzyl aryl ethers 5a – d in 42–70% yields (entries 1–4).…”

mentioning

confidence: 99%

Copper-Catalyzed N- and O-Alkylation of Amines and Phenols using Alkylborane Reagents

2013

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confidence: 99%

Copper-Catalyzed N- and O-Alkylation of Amines and Phenols using Alkylborane Reagents

2013

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“…Williamson ether synthesis reactions 6 and Chan–Lam oxidative coupling reactions, 7 etc. , have limited applications in the synthesis of oxime ethers because these reactions generally require harsh conditions such as high temperatures and strong bases, and they use prefunctionalized substrates.…”

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confidence: 99%

Visible light-triggered synthesis of oxime ethers using tetrabromomethane as a mediator

Chen

Rukhsana

et al. 2022

New J. Chem.

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Catalytic and Base‐free Suzuki‐type α‐Arylation of Cyclic 1,3‐Dicarbonyls via a Cyclic Iodonium Ylide Strategy

Liang,

He,

Zhong

et al. 2024

Angewandte Chemie

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To date, it remains challenging to achieve a general and catalytic α‐arylation of cyclic 1,3‐dicarbonyls, particularly ubiquitous heteroaromatic ones. In most cases, the preparation of their medically significant arylated derivatives requires multistep synthetic sequences. Herein, we introduce a new, convenient strategy involving the conversion of cyclic 1,3‐dicarbonyls to cyclic iodonium ylides (CIYs), followed by rhodium‐catalyzed α‐arylation with arylboronic reagents via carbene coupling. This approach is mild, operationally simple, base‐free, biocompatible, and exhibits broad substrate scope (> 100 examples), especially with respect to various heteroaromatic 1,3‐dicarbonyls and ortho‐substituted or base‐sensitive arylboronic acids. Importantly, owing to the excellent compatibility with various arylboronic acids or boronate esters (ArBpin, ArBneop, or ArBF3K), this method allows the late‐stage installation of heterocyclic 1,3‐dicarbonyl motifs in highly complex settings. The utility of this transformation is further demonstrated through significantly simplifying the synthesis of several bioactive molecules and natural products.

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Expedient Synthesis of Biologically Potent Aryloxycoumarins and (Aryloxyimino)ethylcoumarins via Copper(II)-Promoted Chan–Lam Coupling Reaction

Cited by 12 publications

References 14 publications

Copper-Catalyzed N- and O-Alkylation of Amines and Phenols using Alkylborane Reagents

Copper-Catalyzed N- and O-Alkylation of Amines and Phenols using Alkylborane Reagents

Visible light-triggered synthesis of oxime ethers using tetrabromomethane as a mediator

Catalytic and Base‐free Suzuki‐type α‐Arylation of Cyclic 1,3‐Dicarbonyls via a Cyclic Iodonium Ylide Strategy

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