Carbon–carbon (CC) bond-forming reactions are of paramount importance in organic synthesis, as they play a pivotalrole in the elaboration and extension of organic moleculeframeworks. Among them, C(sp3)–C(sp3) cross-couplingsare generally more challenging than others.

Recently, the part of works of Huang Hai and Sun Jianwei's group was focused on the transformations of oxetanes. This research would achieve the construction of organic skeletons with high value base on the electrophilic property of oxetanes. As a lasted work of Huang Hai and Sun Jianwei's group, a mild ring-opening oxetane by soft carbon nucleophiles has been developed for efficient C-C bond formation.

Up to date, the use of a carbon nucleophile for C-C bond formation has been much less explored. Current success has been limited to the use of strong organometallic reagents (for example, RLi, RMgX), typically in combination with strong Lewis acid activation. In this context, a mild catalytic protocol using soft carbon nucleophiles for ring opening of oxetane has been achieved, in which the product of d-siloxy esters have been used as key intermediates for the synthesis of various natural products. Through the design of molecule, the same strategy could also be applied in intramolecular ring opening of oxetane for the synthesis of natural benzo[b]oxepine deravetives. This work can be treated as an attractive complement to the Mukaiyama aldol and Prins reaction.

The related work of “Mild C–C Bond Formation via Lewis Acid Catalyzed Oxetane Ring Opening with Soft Carbon Nucleophiles” was published on Angew. Chem. Int. Ed. This is the third advance research published by Dr. Huang with high influence.（Ref : 1. Angew. Chem. Int. Ed. 2020, 59, 11245-11249；2. Chem. Sci., 2019, 10, 9586-9590.）

Original Paper Link: https://onlinelibrary.wiley.com/doi/epdf/10.1002/anie.202013062