Catalytic Schmittel-Type [2+2] Cycloaddition of γ-Alkynyl Diazoacetates with Terminal Alkynes for Accessing Cyclobuta[<i>a</i>]indenes
Instead of the conventional [4+2] cycloaddition, a regioselective Schmittel-type [2+2] cycloaddition of yne-allene esters, generated <i>in situ</i> from copper-catalyzed dediazotized coupling of γ-alkynyl diazoacetates with terminal alkynes, is reported, enabling a bicyclization process to produce a diverse array of C<sub>1</sub>-arylated cyclobuta[<i>a</i>]indenes in moderate to good yields. The protocol features wide functional group compatibility, mild reaction conditions, and experimental simplicity, holding significant potential for building new tricyclic cyclobutenes.
Authors
- Wei Hao (ORCID: https://orcid.org/0000-0001-9493-6894)
- Rong Fu (ORCID: https://orcid.org/0000-0001-7791-5805)
- Ke Chen (ORCID: https://orcid.org/0000-0003-2384-8437)
- Yan Zhang (ORCID: https://orcid.org/0000-0002-9173-7029)
- Bo Jiang (ORCID: https://orcid.org/0000-0003-3878-515X)
- Hao Wen (ORCID: https://orcid.org/0000-0002-8407-0369)
- Nan-Nan Wang
Institutions
- Jiangsu Normal University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-03-17
- DOI
- https://doi.org/10.1021/acs.orglett.5c00525
- Citations
- 2
- Primary Topic
- Cyclopropane Reaction Mechanisms
- Type
- article
- Field-Weighted Citation Impact
- 1.87
Funders
- National Natural Science Foundation of China