Addition, Substitution, and Ring-Contraction Reactions of Quinones with N-Heterocyclic Carbenes

Lucy Ping; Jungmin Bak; Youngmee Kim; Jean Bouffard

doi:10.1021/acs.joc.8b01236

Addition, Substitution, and Ring-Contraction Reactions of Quinones with N-Heterocyclic Carbenes

Lucy Ping, Jungmin Bak, Youngmee Kim, Jean Bouffard

Department of Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

3 Scopus citations

Abstract

Despite the common use of quinones as oxidizing agents in N-heterocyclic carbene (NHC)-based organocatalysis and transition-metal catalysis, the direct reactivity of quinones with NHCs remains underexplored. In this paper, we report the reactivity of NHCs with common p- and o-quinones, uncovering three unreported reactions involving contractions of the quinone ring that lead to push-pull furanolactone chromophores, NHC fulvalenes, and α-acylimidazolium cyclopentenone derivatives. These experiments also provide a rationale for the superior compatibility of tetra-tert-alkylated diphenoquinones in NHC-based oxidative transformations.

Original language	English
Pages (from-to)	9240-9249
Number of pages	10
Journal	Journal of Organic Chemistry
Volume	83
Issue number	16
DOIs	https://doi.org/10.1021/acs.joc.8b01236
State	Published - 17 Aug 2018

Bibliographical note

Funding Information:
This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (Grant 2015R1D1A1A01059383). We thank Dr. Hea Kyoung Lee of the Organic Chemistry Research Center at Sogang University for ESI-MS analyses.

Publisher Copyright:
© 2018 American Chemical Society.

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10.1021/acs.joc.8b01236

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title = "Addition, Substitution, and Ring-Contraction Reactions of Quinones with N-Heterocyclic Carbenes",

abstract = "Despite the common use of quinones as oxidizing agents in N-heterocyclic carbene (NHC)-based organocatalysis and transition-metal catalysis, the direct reactivity of quinones with NHCs remains underexplored. In this paper, we report the reactivity of NHCs with common p- and o-quinones, uncovering three unreported reactions involving contractions of the quinone ring that lead to push-pull furanolactone chromophores, NHC fulvalenes, and α-acylimidazolium cyclopentenone derivatives. These experiments also provide a rationale for the superior compatibility of tetra-tert-alkylated diphenoquinones in NHC-based oxidative transformations.",

author = "Lucy Ping and Jungmin Bak and Youngmee Kim and Jean Bouffard",

note = "Funding Information: This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (Grant 2015R1D1A1A01059383). We thank Dr. Hea Kyoung Lee of the Organic Chemistry Research Center at Sogang University for ESI-MS analyses. Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

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doi = "10.1021/acs.joc.8b01236",

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AU - Ping, Lucy

AU - Bak, Jungmin

AU - Kim, Youngmee

AU - Bouffard, Jean

N1 - Funding Information: This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (Grant 2015R1D1A1A01059383). We thank Dr. Hea Kyoung Lee of the Organic Chemistry Research Center at Sogang University for ESI-MS analyses. Publisher Copyright: © 2018 American Chemical Society.

PY - 2018/8/17

Y1 - 2018/8/17

N2 - Despite the common use of quinones as oxidizing agents in N-heterocyclic carbene (NHC)-based organocatalysis and transition-metal catalysis, the direct reactivity of quinones with NHCs remains underexplored. In this paper, we report the reactivity of NHCs with common p- and o-quinones, uncovering three unreported reactions involving contractions of the quinone ring that lead to push-pull furanolactone chromophores, NHC fulvalenes, and α-acylimidazolium cyclopentenone derivatives. These experiments also provide a rationale for the superior compatibility of tetra-tert-alkylated diphenoquinones in NHC-based oxidative transformations.

AB - Despite the common use of quinones as oxidizing agents in N-heterocyclic carbene (NHC)-based organocatalysis and transition-metal catalysis, the direct reactivity of quinones with NHCs remains underexplored. In this paper, we report the reactivity of NHCs with common p- and o-quinones, uncovering three unreported reactions involving contractions of the quinone ring that lead to push-pull furanolactone chromophores, NHC fulvalenes, and α-acylimidazolium cyclopentenone derivatives. These experiments also provide a rationale for the superior compatibility of tetra-tert-alkylated diphenoquinones in NHC-based oxidative transformations.

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Addition, Substitution, and Ring-Contraction Reactions of Quinones with N-Heterocyclic Carbenes

Abstract

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