Cooperative Diarylborinic Acid/Chloride-Catalyzed Formal S<sub>N</sub>i Reaction of <i>cis</i>-4-Hydroxymethyl-1,2-Cyclopentene Oxides
A catalytic formal S<sub>N</sub>i reaction was designed to achieve stereoretentive products for <i>cis</i>-4-hydroxymethyl-1,2-cyclopentene oxides by using diarylborinic acid as a dual role catalyst and chloride as a catalytic transient nucleophile through a double-displacement mechanism. This reaction offers the advantages of a low catalyst loading of 0.1 mol % and wide substrate scope, even including <i>N</i>-substituents. The use of chiral boron acid as a catalyst for this reaction was also attempted.
Authors
- Shan-Shan Xun
- Sheng-Mei Lu (ORCID: https://orcid.org/0009-0001-8858-0841)
- Gao‐Wei Wang
- Yong‐Gui Zhou (ORCID: https://orcid.org/0000-0002-3321-5521)
Institutions
- University of Science and Technology of China (CN)
- Dalian Institute of Chemical Physics (CN)
- Chinese Academy of Sciences (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-09-26
- DOI
- https://doi.org/10.1021/acs.orglett.4c03077
- Citations
- 4
- Primary Topic
- Carbon dioxide utilization in catalysis
- Type
- article
- Field-Weighted Citation Impact
- 0.71
Funders
- National Natural Science Foundation of China
- Dalian Institute of Chemical Physics