Photoactivation of Hydrazones for the Synthesis of Diarylalkanes and Trialkylmethylboronates: The Key Role Played by Soluble Base.
| Autor: | Peng PK; Department of Chemistry, University of Houston, 3585 Cullen Boulevard, Fleming Building 112, Houston, Texas 77204-5003, United States., Donald CP; Department of Chemistry, University of Houston, 3585 Cullen Boulevard, Fleming Building 112, Houston, Texas 77204-5003, United States., Dong Z; Department of Chemistry, University of Houston, 3585 Cullen Boulevard, Fleming Building 112, Houston, Texas 77204-5003, United States., May JA; Department of Chemistry, University of Houston, 3585 Cullen Boulevard, Fleming Building 112, Houston, Texas 77204-5003, United States. |
|---|---|
| Jazyk: | angličtina |
| Zdroj: | Organic letters [Org Lett] 2024 Apr 26; Vol. 26 (16), pp. 3397-3400. Date of Electronic Publication: 2024 Apr 11. |
| DOI: | 10.1021/acs.orglett.4c00873 |
| Abstrakt: | The synthesis of diaryl alkanes and tertiary organoboronates via Barluenga coupling at room temperature occurred via photoactivated conversion of aryl sulfonyl hydrazones to diazo compounds in the presence of soluble bases. The combination of arylsulfonyl hydrazone and a soluble base is necessary to provide a near-UV chromophore. Using aromatic hydrazones and aromatic boronic acids resulted in rapid deboronation because of the instability of dibenzylic boron intermediates. Alkyl hydrazones allowed the isolation of derivatives of the tertiary boronate. |
| Databáze: | MEDLINE |
| Externí odkaz: |
|