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Synthesis 2023; 55(09): 1460-1466
DOI: 10.1055/a-2003-3207
paper

Ruthenium-Catalyzed Regioselective Synthesis of C3-Alkylated Indoles Following Transfer Hydrogenation or Borrowing Hydrogen Strategy

Xia Chen
a   School of Chemistry and Materials Engineering, Liupanshui Normal University, Liupanshui 553004, P. R. of China
b   Guizhou Key Laboratory of Coal Clean Utilization, Liupanshui 553004, P. R. of China
,
Xiao-Yu Zhou∗
a   School of Chemistry and Materials Engineering, Liupanshui Normal University, Liupanshui 553004, P. R. of China
b   Guizhou Key Laboratory of Coal Clean Utilization, Liupanshui 553004, P. R. of China
› Author AffiliationsThe authors are grateful to National Natural Science Foundation of China (Nos. 22062012 and 22262019) and Scientific Research Projects of Liupanshui Normal University (LPSSYZDZK202201) for their financial support. This work was also supported by Guizhou Key Laboratory of Coal Clean Utilization (qiankehepingtairencai [2020]2001).
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Abstract

By employing either borrowing hydrogen or transfer hydrogenation strategy, two straightforward [Ru(p-cymene)Cl2]2-catalyzed methods for regioselective synthesis of C3-alkylated indoles have been developed, utilizing alcohols as H atom donors or alkylating agents. The developed catalytic system could accommodate a broad substrate scope including primary/secondary aliphatic alcohols and substituted indoles, and in most cases providing good yields. Notable features of the developed system include high-activity, easy operation, and air atmosphere.

Key words

transfer hydrogenation - borrowing hydrogen - alkylation - indoles - alcohols

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2003-3207.
  • Supporting Information


Publication History

Received: 01 December 2022

Accepted after revision: 22 December 2022

Accepted Manuscript online:
22 December 2022

Article published online:
12 January 2023

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