Exploring Diversified Synthesis Pathways from Bicyclo[1.1.0]butanes (BCBs) and Benzoquinone Esters to Bicyclo[2.1.1]hexanes (BCHs) and Oxa-bicyclo[3.1.1]heptanes (Oxa-BCHeps)
Lewis acid-catalyzed diverse cyclizations of bicyclo[1.1.0]butanes (BCBs) with benzoquinone esters are reported. Yb(OTf)<sub>3</sub> catalysis enabled a (3 + 2) cyclization to yield quinoid-fused BCHs. In contrast, NdCl<sub>3</sub> catalysis led to the formation of spiro-cyclobutene-benzofuran-2(3<i>H</i>)-one skeletons. Notably, in the presence of Tf<sub>2</sub>NH, quinoid-fused bicyclo[2.1.1]hexanes (BCHs) rearranged to oxa-bicyclo[3.1.1]heptanes (oxa-BCHeps) in moderate to good yields. This (3 + 2) cyclization and rearrangement can be efficiently accomplished in a one-pot, two-step procedure.
Authors
- Li‐Na Guo (ORCID: https://orcid.org/0000-0002-9789-6952)
- Shanghui Tian
- Yinuo Liu (ORCID: https://orcid.org/0009-0008-7124-9328)
- Xin‐Hua Duan (ORCID: https://orcid.org/0000-0002-1527-5934)
- Kuan Zhang (ORCID: https://orcid.org/0000-0002-4262-153X)
- Yan Xia (ORCID: https://orcid.org/0000-0002-9242-2213)
- Zhengyang Gao
Institutions
- Xi'an Jiaotong University (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-09-22
- DOI
- https://doi.org/10.1021/acs.joc.5c01793
- Primary Topic
- Oxidative Organic Chemistry Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.00