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Updated: Jul 4, 2026

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
Published on: December 16, 2019
An intra/intermolecular suzuki sequence to benzopyridyloxepines containing geometrically pure exocyclic
Matthew W Carson1, Matthew W Giese, Michael J Coghlan
1Discovery Chemistry Research and Technology, Lilly Research Laboratories, Eli Lilly and Company, Indianapolis, Indiana 46285, USA. carsonma@lilly.com
Abstract:
A route to enable the preparation of 5-benzylidenyl-benzopyridyloxepine analogues was developed to continue our research in the field of nuclear hormone receptor modulators. The key steps are 1) a syn-stereoselective diboration of a tethered aryl alkyne; 2) an intramolecular Suzuki cross-coupling reaction, which forms in a stereo- and regiocontrolled fashion, the 5-exoalkylidenyl 7-membered ring imbedded within the core of the scaffold and; 3) an intermolecular Suzuki to furnish the final tetra-substituted olefinic benzopyridyloxepines.
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