Generation of Quaternary Carbons in Cycloalkanones and Lactones with Arynes through a Domino Process.

Jih Ru Hwu, Khagendra Prasad Bohara, Mohit Kapoor, Animesh Roy, Shu-Yu Lin, Chun-Cheng Lin, Kuo-Chu Hwang, Wen-Chieh Huang, Shwu-Chen Tsay

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Article in The Journal of organic chemistry, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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9 authors.

Jih Ru HwuDepartment of Chemistry & Frontier Research Center on Fundamental and Applied Sciences of Matters, National Tsing Hua University, Hsinchu 300, Taiwan.ORCID 0000-0002-9225-8484

Khagendra Prasad BoharaDepartment of Chemistry & Frontier Research Center on Fundamental and Applied Sciences of Matters, National Tsing Hua University, Hsinchu 300, Taiwan.

Mohit KapoorDepartment of Chemistry & Frontier Research Center on Fundamental and Applied Sciences of Matters, National Tsing Hua University, Hsinchu 300, Taiwan.

Animesh RoyDepartment of Chemistry & Frontier Research Center on Fundamental and Applied Sciences of Matters, National Tsing Hua University, Hsinchu 300, Taiwan.

Shu-Yu LinInstitute of Biotechnology and Pharmaceutical Research, National Health Research Institutes, Zhunan, Miaoli County 350401, Taiwan.

Chun-Cheng LinDepartment of Chemistry & Frontier Research Center on Fundamental and Applied Sciences of Matters, National Tsing Hua University, Hsinchu 300, Taiwan.ORCID 0000-0002-2323-0920

Kuo-Chu HwangDepartment of Chemistry & Frontier Research Center on Fundamental and Applied Sciences of Matters, National Tsing Hua University, Hsinchu 300, Taiwan.ORCID 0000-0003-1814-9869

Wen-Chieh HuangDepartment of Chemistry & Frontier Research Center on Fundamental and Applied Sciences of Matters, National Tsing Hua University, Hsinchu 300, Taiwan.

Shwu-Chen TsayDepartment of Chemistry & Frontier Research Center on Fundamental and Applied Sciences of Matters, National Tsing Hua University, Hsinchu 300, Taiwan.

Funding

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6 · The paper itself

Abstract

A synthetic method was developed for the generation of a quaternary carbon center in carbonyl compounds. This innovative process involved the reaction of α-thiolate lactones and cycloalkanones with two equivalents of arynes in acetonitrile to give α,α-diarylated products in 63-85% yields at 25 °C. The reaction unfolds through an unconventional domino process, encompassing sequential 1,2-elimination, 1,2-nucleophilic addition, 1,4-proton transfer, the second 1,2-nucleophilic addition, interrupted Pummerer rearrangement, intramolecular spirocyclization, and sulfonium ring-opening. The potential of this "single-flask" reaction was systematically investigated and found well-suited to generate diarylated carbonyl compounds, incorporating naphthalene, pyridine, quinoline, or isoquinoline rings adorned with various substituents.

Identifiers

PMID39614987

DOI10.1021/acs.joc.4c02257

PMCPMC11667720

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