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Photoredox/nickel dual-catalyzed regioselective alkylation of propargylic carbonates for trisubstituted allenes.
Zhou, Zhao-Zhao; Song, Xian-Rong; Du, Sha; Xia, Ke-Jian; Tian, Wan-Fa; Xiao, Qiang; Liang, Yong-Min.
Affiliation
  • Zhou ZZ; College of Chemistry and Food Science, Nanchang Normal University, Nanchang, 330000, P. R. China. zhouzz@lzu.edu.cn.
  • Song XR; State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, 730000, P. R. China. liangym@lzu.edu.cn.
  • Du S; Institute of Organic Chemistry, Jiangxi Science & Technology Normal University, Key Laboratory of Organic Chemistry, Nanchang, 330000, Jiangxi Province, P. R. China. xiaoqiang@tsinghua.org.cn.
  • Xia KJ; Institute of Organic Chemistry, Jiangxi Science & Technology Normal University, Key Laboratory of Organic Chemistry, Nanchang, 330000, Jiangxi Province, P. R. China. xiaoqiang@tsinghua.org.cn.
  • Tian WF; College of Chemistry and Food Science, Nanchang Normal University, Nanchang, 330000, P. R. China. zhouzz@lzu.edu.cn.
  • Xiao Q; Institute of Organic Chemistry, Jiangxi Science & Technology Normal University, Key Laboratory of Organic Chemistry, Nanchang, 330000, Jiangxi Province, P. R. China. xiaoqiang@tsinghua.org.cn.
  • Liang YM; Institute of Organic Chemistry, Jiangxi Science & Technology Normal University, Key Laboratory of Organic Chemistry, Nanchang, 330000, Jiangxi Province, P. R. China. xiaoqiang@tsinghua.org.cn.
Chem Commun (Camb) ; 57(74): 9390-9393, 2021 Sep 16.
Article in En | MEDLINE | ID: mdl-34528958
ABSTRACT
Herein, a highly regioselective alkylation of propargylic carbonates for trisubstituted allenes with alkyl 1,4-dihydropyridine derivatives (1,4-DHPs) is developed via a photoredox/nickel dual-catalyzed process, which represents the first direct approach to access alkylated allene products without alkyl organometallic reagents. This method features a broad substrate scope and mild conditions. A hypothetical mechanism with an alkyl radical and an allenyl Ni(III) species is proposed. Benzylation products were also obtained to be the complement building blocks for the potential synthesis of pharmaceuticals.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Carbonates / Alkadienes / Nickel Language: En Journal: Chem Commun (Camb) Journal subject: QUIMICA Year: 2021 Document type: Article Country of publication: ENGLAND / ESCOCIA / GB / GREAT BRITAIN / INGLATERRA / REINO UNIDO / SCOTLAND / UK / UNITED KINGDOM
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Carbonates / Alkadienes / Nickel Language: En Journal: Chem Commun (Camb) Journal subject: QUIMICA Year: 2021 Document type: Article Country of publication: ENGLAND / ESCOCIA / GB / GREAT BRITAIN / INGLATERRA / REINO UNIDO / SCOTLAND / UK / UNITED KINGDOM