Recyclable Auxiliary Research Articles

Photoreductive N-N Homocoupling Catalyzed by a Superphotoreductant.

Azines are valuable synthons or target molecules in organic synthesis. In this work, we report that CBZ6 could work as a photoreductive catalyst for the N-N homocoupling of oximes in high efficiency. This therefore enabled convenient access to a large variety of azines from the corresponding aryl and alkyl ketones, as well as aryl aldehydes in up to 99% yield. 2,4-Dinitrophenoxyl was used as the recyclable auxiliary and the CBZ6 photocatalyst could also be recycled. These together with the low catalyst loading (2 mol % of CBZ6), the short reaction time (4 h), and the nontoxic DMSO solvent make the current process a sustainable and practical alternative to the classic methods.

Synthesis of 2-Pyrones from Renewable Resources

AbstractAn atom-economic reaction sequence on a multigram scale for synthesizing 2-pyrone was developed starting from furfuryl alcohol, a renewable resource made from bran or bagasse, utilizing a large-scale thermal rearrangement of cyclopentadienone epoxide as the key step. Additionally, 6-substituted 2-pyrone natural product derivatives are readily accessible by this approach.

Synthetic Approach to Benzocyclobutenones Using Visible Light and a Phosphonate Auxiliary.

Reported herein is a two-step procedure to synthesize benzocyclobutenones from (o-alkylbenzoyl)phosphonates. It consists of a visible-light-driven cyclization reaction forming phosphonate-substituted benzocyclobutenols and subsequent elimination reaction of the H-phosphonate, which assumes a key role as the recyclable auxiliary. A wide variety of functionalized benzocyclobutenones, which include those difficult to synthesize by conventional methods, are efficiently synthesized.

A Robust Asymmetric Allylboration of Ketones with a Recyclable Auxiliary

A Robust Asymmetric Allylboration of Ketones with a Recyclable Auxiliary

A Robust and Versatile Allyl- and Crotylboration with a Recyclable Auxiliary

A Robust and Versatile Allyl- and Crotylboration with a Recyclable Auxiliary