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May 2, 20260 citations

Yb(OTf)3-Catalyzed Schmidt-Semipinacol 1,2-Rearrangements of Bicyclo1.1.0butanes with 2-Azidoquinoline 1-Oxides.

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KDKailiang DingGYGuoxin YangJLJing Liu

Key Points

  • To develop a new catalytic process for rearranging bicyclo[1.1.0]butanes into cyclobutenes.
  • Yb(OTf)3 catalysis employed for cascade transformation
  • Bicyclo[1.1.0]butanes reacted with 2-azidoquinoline 1-oxides
  • Analysis conducted on reaction yields and product derivatization.
  • Moderate to high yields of cyclobutenes were achieved
  • Facilitated derivatization showcases product application possibilities
  • Mild reaction conditions underscore utility for further synthetics.

Abstract

-catalyzed cascade transformation has been developed, enabling the strain-release driven 1,2-rearrangement of bicyclo1.1.0butanes (BCBs) with 2-azidoquinoline 1-oxides via a Schmidt-type interruption and a subsequent semipinacol rearrangement process. This reaction offers a mild and novel access to highly substituted cyclobutenes in moderate to high yields. The protocol's scalability and the facile derivatization of the products underscore its application potential.

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Cite This Study

Ding et al. (2026) studied this question.

synapsesocial.com/papers/69f5943c71405d493afff09fhttps://doi.org/10.1021/acs.orglett.6c01204
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