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2,2'-Biphenol/B(OH)3 Catalyst System for Nazarov Cyclization.

Kenji Sugimoto1, Miyu Oshiro1, Ryuhei Hada1

  • 1Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama.

Chemical & Pharmaceutical Bulletin
|September 3, 2019
PubMed
Summary
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A new catalyst system using 2,2'-biphenol and boric acid promotes Nazarov cyclization for cyclopentenone synthesis. This eco-friendly method offers high yields and cis-selectivity under mild conditions.

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Green Chemistry

Background:

  • The Nazarov cyclization is a key reaction for synthesizing cyclopentenones.
  • Traditional methods often require harsh conditions and hazardous reagents, limiting their practical application.

Purpose of the Study:

  • To develop a novel, efficient, and environmentally friendly catalyst system for the Nazarov cyclization.
  • To synthesize cyclopentenones from activated and inactivated divinyl ketones using readily available and safe reagents.

Main Methods:

  • Utilized a catalyst system composed of 2,2 '-biphenol and boric acid (B(OH)3).
  • Applied the catalyst to the Nazarov cyclization of various activated and inactivated divinyl ketones.
  • Optimized reaction conditions for yield and cis-selectivity.
Keywords:
2,2′-biphenolNazarov cyclizationboric acidcyclopentenone

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Main Results:

  • Achieved high yields of cyclopentenones, up to 96%.
  • Demonstrated excellent cis-selectivity in the cyclization products.
  • Established a user-friendly method using bench-stable and easy-to-handle reagents.

Conclusions:

  • The novel 2,2 '-biphenol/boric acid catalyst system provides an efficient and green alternative for Nazarov cyclization.
  • This method avoids harsh conditions and toxic reagents, making it suitable for broader applications in organic synthesis.