Yb(OTf) <sub>3</sub> -Catalyzed Schmidt-Semipinacol [1,2]-Rearrangements of Bicyclo[1.1.0]butanes with 2-Azidoquinoline 1-Oxides

-catalyzed cascade transformation has been developed, enabling the strain-release driven [1,2]-rearrangement of bicyclo[1.1.0]butanes (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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Publication Details

Journal
Organic Letters
Published
2026-04-30
DOI
https://doi.org/10.1021/acs.orglett.6c01204
Primary Topic
Cyclopropane Reaction Mechanisms
Type
article
Field-Weighted Citation Impact
0.00

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article

Yb(OTf) 3 -Catalyzed Schmidt-Semipinacol [1,2]-Rearrangements of Bicyclo[1.1.0]butanes with 2-Azidoquinoline 1-Oxides

Manman Sun, Maozhong Miao, Junying Zhang, Guoxin Yang et al.
Organic Letters
Cyclopropane Reaction Mechanisms
article

Yb(OTf) 3 -Catalyzed Schmidt-Semipinacol [1,2]-Rearrangements of Bicyclo[1.1.0]butanes with 2-Azidoquinoline 1-Oxides

Manman Sun, Maozhong Miao, Junying Zhang, Guoxin Yang, Jing Liu, Kailiang Ding
article en

Abstract

-catalyzed cascade transformation has been developed, enabling the strain-release driven [1,2]-rearrangement of bicyclo[1.1.0]butanes (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.

Organic Letters
Zhejiang Sci-Tech University (CN), Advanced Research Institute (US), Taizhou University (CN)
Natural Science Foundation of Zhejiang Province
Openalex Percentile: Top 14%
Cyclopropane Reaction Mechanisms
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