Unactivated C(sp3)–H Bond Functionalization of Alkyl Nitriles with Vinylarenes and Mechanistic Studies
The first example of a metal-free unactivated C(sp3)–H bond functionalization of alkyl nitriles with terminal vinylarenes to provide γ-ketonitrile derivatives is described. This protocol features simple operations, a broad substrate scope, and atom and step economy. In addition, Cu-catalyzed C(sp3...
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| Published in | Organic letters Vol. 18; no. 23; pp. 5986 - 5989 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
02.12.2016
Amer Chemical Soc |
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| Abstract | The first example of a metal-free unactivated C(sp3)–H bond functionalization of alkyl nitriles with terminal vinylarenes to provide γ-ketonitrile derivatives is described. This protocol features simple operations, a broad substrate scope, and atom and step economy. In addition, Cu-catalyzed C(sp3)–H bond functionalization of azodiisobutyronitrile (AIBN) and analogues with terminal vinylarenes to generate γ-ketonitriles was also studied. A preliminary free-radical pathway was confirmed by capturing an alkyl radical, and a conjugate system was found that can stabilize radical intermediates and be in favor of this transformation. Density functional theory (DFT) calculations also provide important evidence of the free-radical pathway. |
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| AbstractList | The first example of a metal-free unactivated C(sp³)–H bond functionalization of alkyl nitriles with terminal vinylarenes to provide γ-ketonitrile derivatives is described. This protocol features simple operations, a broad substrate scope, and atom and step economy. In addition, Cu-catalyzed C(sp³)–H bond functionalization of azodiisobutyronitrile (AIBN) and analogues with terminal vinylarenes to generate γ-ketonitriles was also studied. A preliminary free-radical pathway was confirmed by capturing an alkyl radical, and a conjugate system was found that can stabilize radical intermediates and be in favor of this transformation. Density functional theory (DFT) calculations also provide important evidence of the free-radical pathway. The first example of a metal-free unactivated C(sp(3))-H bond functionalization of alkyl nitriles with terminal vinylarenes to provide gamma-ketonitrile derivatives is described. This protocol features simple operations, a broad substrate scope, and atom and step economy. In addition, Cu-catalyzed C(sp(3))-H bond functionalization of azodi-isobutyronitrile (AIBN) and analogues with terminal vinylarenes to generate gamma-ketonitriles was also studied. A preliminary free-radical pathway was confirmed by capturing an alkyl radical, and a conjugate system was found that can stabilize radical intermediates and be in favor of this transformation. Density functional theory (DFT) calculations also provide important evidence of the free-radical pathway. The first example of a metal-free unactivated C(sp3)–H bond functionalization of alkyl nitriles with terminal vinylarenes to provide γ-ketonitrile derivatives is described. This protocol features simple operations, a broad substrate scope, and atom and step economy. In addition, Cu-catalyzed C(sp3)–H bond functionalization of azodiisobutyronitrile (AIBN) and analogues with terminal vinylarenes to generate γ-ketonitriles was also studied. A preliminary free-radical pathway was confirmed by capturing an alkyl radical, and a conjugate system was found that can stabilize radical intermediates and be in favor of this transformation. Density functional theory (DFT) calculations also provide important evidence of the free-radical pathway. The first example of a metal-free unactivated C(sp )-H bond functionalization of alkyl nitriles with terminal vinylarenes to provide γ-ketonitrile derivatives is described. This protocol features simple operations, a broad substrate scope, and atom and step economy. In addition, Cu-catalyzed C(sp )-H bond functionalization of azodiisobutyronitrile (AIBN) and analogues with terminal vinylarenes to generate γ-ketonitriles was also studied. A preliminary free-radical pathway was confirmed by capturing an alkyl radical, and a conjugate system was found that can stabilize radical intermediates and be in favor of this transformation. Density functional theory (DFT) calculations also provide important evidence of the free-radical pathway. The first example of a metal-free unactivated C(sp3)-H bond functionalization of alkyl nitriles with terminal vinylarenes to provide γ-ketonitrile derivatives is described. This protocol features simple operations, a broad substrate scope, and atom and step economy. In addition, Cu-catalyzed C(sp3)-H bond functionalization of azodiisobutyronitrile (AIBN) and analogues with terminal vinylarenes to generate γ-ketonitriles was also studied. A preliminary free-radical pathway was confirmed by capturing an alkyl radical, and a conjugate system was found that can stabilize radical intermediates and be in favor of this transformation. Density functional theory (DFT) calculations also provide important evidence of the free-radical pathway. |
| Author | Bai, Cui-Bing Lan, Cui-Lan Zhang, Tong Wang, Nai-Xing Chen, Shi-Lu Lan, Xing-Wang Xing, Yalan |
| AuthorAffiliation | Department of Chemistry Chinese Academy of Sciences Technical Institute of Physics and Chemistry & University of Chinese Academy of Sciences William Paterson University of New Jersey School of Chemistry Beijing Institute of Technology |
| AuthorAffiliation_xml | – name: Technical Institute of Physics and Chemistry & University of Chinese Academy of Sciences – name: Department of Chemistry – name: Chinese Academy of Sciences – name: Beijing Institute of Technology – name: School of Chemistry – name: William Paterson University of New Jersey |
| Author_xml | – sequence: 1 givenname: Xing-Wang surname: Lan fullname: Lan, Xing-Wang – sequence: 2 givenname: Nai-Xing surname: Wang fullname: Wang, Nai-Xing email: nxwang@mail.ipc.ac.cn – sequence: 3 givenname: Cui-Bing surname: Bai fullname: Bai, Cui-Bing – sequence: 4 givenname: Cui-Lan surname: Lan fullname: Lan, Cui-Lan – sequence: 5 givenname: Tong surname: Zhang fullname: Zhang, Tong – sequence: 6 givenname: Shi-Lu surname: Chen fullname: Chen, Shi-Lu email: shlchen@bit.edu.cn – sequence: 7 givenname: Yalan surname: Xing fullname: Xing, Yalan email: xingy@wpunj.edu |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/27934364$$D View this record in MEDLINE/PubMed |
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| Keywords | KETONES ACTIVATED ALKENES CINNAMIC-ACIDS METAL-FREE CONDITIONS ALLYLIC ALCOHOLS ALPHA COPPER RADICAL-ADDITION C-H BONDS ALKENYLATION |
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| Snippet | The first example of a metal-free unactivated C(sp3)–H bond functionalization of alkyl nitriles with terminal vinylarenes to provide γ-ketonitrile derivatives... The first example of a metal-free unactivated C(sp(3))-H bond functionalization of alkyl nitriles with terminal vinylarenes to provide gamma-ketonitrile... The first example of a metal-free unactivated C(sp )-H bond functionalization of alkyl nitriles with terminal vinylarenes to provide γ-ketonitrile derivatives... The first example of a metal-free unactivated C(sp3)-H bond functionalization of alkyl nitriles with terminal vinylarenes to provide γ-ketonitrile derivatives... The first example of a metal-free unactivated C(sp³)–H bond functionalization of alkyl nitriles with terminal vinylarenes to provide γ-ketonitrile derivatives... |
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| SubjectTerms | chemical reactions chemical structure Chemistry Chemistry, Organic methodology nitriles Physical Sciences Science & Technology |
| Title | Unactivated C(sp3)–H Bond Functionalization of Alkyl Nitriles with Vinylarenes and Mechanistic Studies |
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