Copper-Catalyzed Borylative Ring Closing C-C Coupling toward Spiro- and Dispiroheterocycles

Jordi Royes, Shaofei Ni, Albert Farré, Enrico La Cascia, Jorge J. Carbó, Ana B. Cuenca, Feliu Maseras, Elena Fernández

Research output: Indexed journal article Articlepeer-review

34 Citations (Scopus)

Abstract

The synthesis of spiroheterocyclic structures with a pendant methylene boronate substituent has been accomplished to promote further functionalization. A Cu-catalyzed borylative ring closing C-C coupling of an alkenyl halide is the key step toward the synthesis of [m.n]-spirocycles (m,n = 3-5). Computational studies on the mechanism reproduced all the experimental trends and explain the enhanced reactivity of systems leading to strained smaller rings. The optimized protocol also gives access to dispirocycle scaffolds, fully characterized by X-ray diffraction.

Original languageEnglish
Pages (from-to)2833-2838
Number of pages6
JournalACS Catalysis
Volume8
Issue number4
DOIs
Publication statusPublished - 6 Apr 2018

Fingerprint

Dive into the research topics of 'Copper-Catalyzed Borylative Ring Closing C-C Coupling toward Spiro- and Dispiroheterocycles'. Together they form a unique fingerprint.

Cite this