Synthesis 2021; 53(13): 2212-2218
DOI: 10.1055/a-1331-7346
paper

Mild and Efficient Copper-Catalyzed Synthesis of Trisubstituted Pyrroles

Authors

  • Ming-Hua Hsu

    a   Department of Chemistry, National Changhua University of Education, Changhua 50007, Taiwan
  • Mohit Kapoor

    b   Chitkara University Institute of Engineering and Technology, Chitkara University, Punjab 140 401, India
  • Tapan Kumar Pradhan

    c   Department of Chemistry and Frontier Research Center on Fundamental & Applied Sciences of Matters, National Tsing Hua University, Hsinchu 30013, Taiwan
  • Man-Him Tse

    a   Department of Chemistry, National Changhua University of Education, Changhua 50007, Taiwan
  • Hsin-Ya Chen

    a   Department of Chemistry, National Changhua University of Education, Changhua 50007, Taiwan
  • Man-Jun Yan

    a   Department of Chemistry, National Changhua University of Education, Changhua 50007, Taiwan
  • Yu-Tsen Cheng

    a   Department of Chemistry, National Changhua University of Education, Changhua 50007, Taiwan
  • Yu-Cheng Lin

    a   Department of Chemistry, National Changhua University of Education, Changhua 50007, Taiwan
  • Cheng-Ying Hsieh

    d   Department of Chemistry, National Tsing Hua University, Hsinchu 30013, Taiwan
  • Ker-Yin Liu

    d   Department of Chemistry, National Tsing Hua University, Hsinchu 30013, Taiwan
  • Chien-Chung Han

    d   Department of Chemistry, National Tsing Hua University, Hsinchu 30013, Taiwan

The project was supported by the Ministry of Science and Technology (MOST 106-2113-M -018-008, MOST 107-2113-M-018-008, MOST 108-2113-M-018-009). M. Kapoor thanks the Start-up funding from Chitkara University and Chitkara University Research and Innovation Network.


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Abstract

A sustainable and time economic approach has been developed for the synthesis of polysubstituted pyrroles using copper iodide as a catalyst. The reaction proceeded through imine formation followed by cyclization with alkyne-Cu intermediate, which was supported by control experiments studies. The newly formed substituted pyrroles were obtained in excellent yields with high regioselectivity under mild conditions.

Supporting Information



Publication History

Received: 24 September 2020

Accepted after revision: 07 December 2020

Accepted Manuscript online:
07 December 2020

Article published online:
02 March 2021

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